CN115819387A - Synthesis method of stereospecific hydroxypropyl tetrahydropyrane triol - Google Patents
Synthesis method of stereospecific hydroxypropyl tetrahydropyrane triol Download PDFInfo
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Abstract
The invention provides a synthesis method of stereospecific hydroxypropyl tetrahydropyrane triol, belonging to the technical field of organic synthesis. The synthesis method comprises the following steps: (1) Taking the compound 1 as a raw material, and carrying out Knoevenagel condensation reaction with acetylacetone in a water phase to prepare a compound 2; (2) In an isopropanol system, the compound 2 is subjected to a hydrogen transfer reaction promoted by a catalyst under an alkaline condition, and the compound 3, namely the S-configuration vitronectin is obtained through reduction. The synthesis method adopts a specific chiral catalyst for regulation and control, and realizes efficient and stereospecific reduction of beta-xylopyranoside by utilizing metal-catalyzed hydrogen transfer reaction to obtain the specific S-configuration vitronectin. The synthetic method has the advantages of simple operation steps, mild reaction conditions, easy post-treatment, good safety and the like, and the prepared S-shaped vitreous color factor has high yield and high purity and has the potential of industrial production of the S-shaped vitreous color factor.
Description
Technical Field
The invention belongs to the technical field of organic synthesis, and particularly relates to a synthetic method of stereospecific hydroxypropyl tetrahydropyrane triol.
Background
Glassy cause, INCI (International nomenclature for cosmetic materials) named hydroxypropyl tetrahydropyrane triol, was originally a bioactive substance derived from natural xylose by Irya, and has the effect of resisting skin aging. The mechanism of action of vitronectin for resisting aging is mainly embodied in that synthesis of glycosaminoglycan GAGs is stimulated, hyaluronic acid and collagen are promoted to be generated, adhesion between dermis and epidermis is improved, regeneration of damaged tissues is promoted, elasticity of dermis is maintained, and skin aging is prevented (Guo Li, chinese cosmetics 2020,10,80.).
The hydroxypropyl tetrahydropyrane triol has various stereo configurations, wherein the compound of CAS NO.439685-79-7 is racemate thereof, and the structure is
The compound of CAS NO.868156-46-1 is in S configuration and has the structure of
Patent and research article Synthesis of Pro-Xylane with publication number CN100441588C TM The A new biological active C-glycoside in aqueous media (DOI: 10.1016/j. Bmcl.2008.12.037) shows that the activity of the S-configuration hydroxypropyl tetrahydropyrane triol (S-bosity) is optimal.
The original preparation method for synthesizing the bosity by taking D-xylose as an initial raw material is disclosed for the first time in 2002 by Eriya, but the preparation method has the problems of long reaction time, poor stereochemical selectivity and the like. In 2009, the team further refined previous work, shortened reaction times and improved stereochemical selectivity (bioorg. Med. Chem. Lett.2009,19,845).
Recently, other synthetic methods for vitronectin have also been reported successively. Patent application with publication number CN113735811a discloses a method for synthesizing a vitreous chromogen by acylation protection and reduction, the method needs acylation reaction to acylate three hydroxyls in a first intermediate product to obtain an intermediate triester, the intermediate triester is extracted and separated, an alpha configuration product is removed by recrystallization, and a ketone carbonyl and an ester group can be simultaneously reduced by a strong reducing agent to obtain an S-vitreous chromogen, but the method needs three steps, is relatively complex, and has a low yield of the prepared S-vitreous chromogen. The patent application with the publication number of CN113735810A reports a method for synthesizing the vitronectin by acetal/ketal protection and reduction, and the method also has the problem of complicated preparation process. Patent application publication No. CN112812087A utilizes nucleophilic addition and 1,4-Michael addition tandem reaction to synthesize a vitreous color factor, but the obtained vitreous color is racemic body, and an S-vitreous color factor cannot be obtained. Patent application with publication number CN110467591a reports a method for synthesizing a vitreous chromogen by a one-pot method of xylose and ethyl acetoacetate promoted by rare earth metal complexes; the patent application with the publication number of CN111876452A discloses a method for preparing a vitronectin by using isopropanol dehydrogenase and a vitronectin one-pot method; the patent application with the publication number of CN114835666A takes D-xylose as a raw material and prepares the vitreous chromogen through two-step full-continuous reaction, but the method can only obtain racemate and cannot obtain S-vitreous chromogen.
At present, methods for synthesizing the vitreochrome are reported, and selective construction of stereospecific S-vitreochrome is rarely realized through a catalytic strategy. For example, in patent application No. CN114835666a, ruthenium carbon is used as an inorganic metal catalyst to catalyze, only racemic form is produced, and S-configuration vitreous form cannot be synthesized. Therefore, it is necessary to develop a simple and efficient catalytic method suitable for commercial mass production of stereospecific vitreous chromogens, so as to meet the market demand for S-configuration vitreous chromogens.
Disclosure of Invention
The invention aims to provide a method for preparing stereospecific hydroxypropyl tetrahydropyran triol (vitriol) with easy operation, mild reaction and commercial large-scale production potential.
The invention provides a synthesis method of stereospecific hydroxypropyl tetrahydropyrane triol, which comprises the following steps:
(1) Taking compound 1D-xylose as a raw material, and carrying out Knoevenagel condensation reaction with acetylacetone in a water phase to prepare compound 2 beta-acetone xyloside;
(2) In an isopropanol system, promoting hydrogen transfer reaction of beta-xyloside by a catalyst under an alkaline condition to realize reduction of the beta-xyloside to obtain a compound 3S configuration vitronectin.
Further, in the step (1), the water phase is an aqueous alkali solution; preferably, the concentration of the alkali is 1 to 5mol/L.
Further, in the step (1), the molar ratio of the D-xylose to the acetylacetone is 1:1.0 to 4.0; preferably 1:1.0 to 2.0;
and/or in the step (1), the molar ratio of the D-xylose to the alkali is 1:1.0 to 4.0; preferably 1:1.0 to 3.0.
Further, in the step (1), the alkali is any one or more of sodium carbonate, sodium hydroxide, potassium hydroxide and sodium bicarbonate.
Further, in the step (2), the isopropanol system is an isopropanol solvent or a mixed solvent containing isopropanol.
Further, in the step (2), the volume ratio of the isopropanol to other solvents is 1:0.1 to 10;
preferably, the other solvent is any one or more of water, isopropanol, methanol, ethanol and tetrahydrofuran.
Further, in the step (2), the molar ratio of the beta-acetone xyloside to the catalyst to the base is 1:0.01 to 0.1:0.01 to 0.2; preferably 1:0.01 to 0.05:0.01 to 0.1.
Further, in the step (2), the catalyst is one or more of Noyori (S, S) -ruthenium catalyst.
Further, in the step (2), the catalyst is one or more of cat.a, cat.b and cat.c:
further, in the step (1), the temperature of the Knoevenagel condensation reaction is 0-90 ℃; the reaction temperature is preferably 30-70 ℃;
and/or in the step (2), the temperature of the hydrogen transfer reaction is 0-120 ℃; the reaction temperature is preferably 25 to 60 ℃.
Compared with the prior art, the invention has the following beneficial effects:
(1) The method avoids the use of a carbonyl reduction reagent with a dosage, so that the reaction condition is mild, and potential safety hazards in industrial production are further eliminated compared with the conventional carbonyl reduction reaction.
(2) When the S-boscalid is prepared in the prior art, the yield and the stereoselectivity cannot be simultaneously considered; when the organic ruthenium complex is used as the catalyst to prepare the S-boscalid, the yield is basically over 90 percent, and the stereospecificity and high yield are both considered.
(3) The method utilizes the chiral catalyst to efficiently regulate and control, prepares the stereospecific hydroxypropyl tetrahydropyrane triol (vitriol), is convenient for separating and purifying the product, and has good application prospect and promising economic benefit.
In conclusion, the invention provides a synthesis method of stereospecific hydroxypropyl tetrahydropyran triol (vitronectin), which adopts a specific chiral catalyst for regulation and control, utilizes a metal-catalyzed hydrogen transfer reaction to realize efficient and stereospecific reduction of beta-acetone xyloside, and obtains the specific S-configuration vitronectin. The synthetic method has the advantages of simple operation steps, mild reaction conditions, easy post-treatment, good safety and the like, and the prepared S-shaped vitreous color factor has high yield and high purity and has the potential of industrial production of the S-shaped vitreous color factor.
Obviously, many modifications, substitutions, and variations are possible in light of the above teachings of the invention, without departing from the basic technical spirit of the invention, as defined by the following claims.
The present invention will be described in further detail with reference to the following examples. This should not be understood as limiting the scope of the above-described subject matter of the present invention to the following examples. All the technologies realized based on the above contents of the present invention belong to the scope of the present invention.
Detailed Description
The raw materials and equipment used in the embodiment of the present invention are known products and commercially available products.
The structures of the ruthenium catalysts used in the embodiments of the present invention are respectively as follows:
example 1 preparation of S-configuration vitronectin by the method of the invention
52.0g of NaOH (1.3 mol) are admixed with H 2 O (1.2L) was added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, and then 150.13g D-xylose (1.0 mol) was added, and stirring was continued until dissolved. At room temperature, after adding 120.13g acetylacetone (1.2 mol), the internal temperature is raised to 70 ℃, and TCL monitors in real time until the D-xylose reaction is complete. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 171.50g of crude product beta-xylopyranoside with the yield of about 90.20%.
171.12g crude beta-xyloside acetonide (0.9 mol), 11.43g ruthenium catalyst cat.A (18 mmol), 2.01g potassium hydroxide (36 mmol) were added to a reaction flask, nitrogen was substituted three times, 30mL isopropanol and 300mL methanol were added, stirring was raised to 50 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while the solution is hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-vitreochrome 160.62g, the yield 92.91%, and the HPLC purity is 99%.
Example 2 preparation of S-configuration vitronectin by the method of the invention
137.80g sodium carbonate (1.3 mol) and water (1.2L) were added to a 2.0L reaction flask, placed in an ice bath, stirred for clearing, added 150.13g D-xylose (1.0 mol), and stirred continuously until clear. At room temperature, 150.13g acetylacetone (1.5 mol) is added, the internal temperature is raised to 90 ℃, and TCL is monitored in real time until the D-xylose reaction is completed. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml x 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 150.50g of crude beta-xylopyranoside with the yield of about 79.26%.
150.0g of crude beta-xylopyranoside (0.79 mol), 8.39g of ruthenium catalyst cat.B (15.8 mmol) and 1.77g of potassium hydroxide (31.6 mmol) were added to a reaction flask, nitrogen was replaced three times, 30mL of isopropanol and 300mL of tetrahydrofuran were added, the mixture was stirred and heated to 50 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while the solution is hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-vitreochrome 142.65g, the yield is 94.4%, and the HPLC purity is 99%.
Example 3 preparation of S-configuration vitronectin by the method of the invention
52.0g of NaOH (1.3 mol) are admixed with H 2 O (1.2L) was added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, 150.13g D-xylose (1.0 mol) was added, and stirring was continued until dissolved. At room temperature, after adding 120.13g acetylacetone (1.2 mol), the internal temperature is raised to 70 ℃, and TCL is monitored in real time until the D-xylose reaction is complete. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml x 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 171.50g of crude product beta-xylopyranoside with the yield of about 90.2%.
150.0g of crude beta-xylopyranoside (0.79 mol), 10.29g of ruthenium catalyst cat.C (15.8 mmol) and 1.77g of potassium hydroxide (31.6 mmol) were added to a reaction flask, nitrogen was replaced three times, 600mL of isopropanol was added, the mixture was stirred and heated to 50 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 40 ℃ to dissolve until the solid is basically dissolved, filtering while the solution is hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-vitreochrome 140.65g, the yield is 93.1%, and the HPLC purity is 99%.
Example 4 preparation of S-configuration vitronectin by the method of the invention
252.0g of sodium hydrogencarbonate (3.0 mol) were admixed with H 2 O (1.2L) was added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, and then 150.13g D-xylose (1.0 mol) was added, and stirring was continued until dissolved. At room temperature, 150.13g acetylacetone (1.5 mol) is added, the internal temperature is raised to 70 ℃, and TCL is monitored in real time until the D-xylose reaction is complete. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 150.12g of crude product beta-xylopyranoside with the yield of about 79.1%.
150.0g of crude beta-acetonyloside (0.79 mol), 5.14g of ruthenium catalyst cat. C (7.9 mmol) and 1.77g of potassium hydroxide (31.6 mmol) were added to a reaction flask, nitrogen was replaced three times, 400mL of isopropanol and 200mL of water were added, the mixture was stirred and heated to 70 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while the solution is hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-vitreochrome 138.62g, the yield is 91.8%, and the HPLC purity is 99%.
Example 5 preparation of S-configuration vitronectin by the method of the invention
137.8g of sodium carbonate (1.3 mol) and water (1.2L) were added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, added with 150.13g D-xylose (1.0 mol), and stirred continuously until dissolved. At room temperature, 150.13g acetylacetone (1.5 mol) is added, the internal temperature is raised to 90 ℃, and TCL is monitored in real time until the D-xylose reaction is complete. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 150.50g of crude product beta-xylopyranoside with the yield of about 79.2%.
150.0g of crude beta-xylopyranoside (0.79 mol), 20.91g of ruthenium catalyst cat.B (39.5 mmol) and 3.16g of sodium hydroxide (79.0 mmol) were added to a reaction flask, nitrogen was replaced three times, 300mL of isopropanol and 100mL of water were added, the mixture was stirred and heated to 50 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-boscalid 142.65g, the yield is 94.4%, and the HPLC purity is 99%.
Example 6 preparation of S-configuration vitronectin by the method of the invention
84g of potassium hydroxide (1.5 mol) are reacted with H 2 O (1.2L) was added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, and then 150.13g D-xylose (1.0 mol) was added, and stirring was continued until dissolved. At room temperature, 200.13g of acetylacetone (2.0 mol) was added, the internal temperature was raised to 40 ℃ and TCL was monitored in real time until the D-xylose reaction was complete. After the reaction is finished, the temperature is reduced to room temperature, and the pH value is adjusted to 5 by hydrochloric acid. Ethyl acetate extraction (300ml x 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying with ethanol (450ml x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 163.12g of crude product beta-xylopyranoside with the yield of about 85.8%.
150.0g of crude beta-xylopyranoside (0.79 mol), 5.14g of ruthenium catalyst cat.C (7.9 mmol) and 1.26g of sodium hydroxide (31.6 mmol) were added to a reaction flask, nitrogen was replaced three times, 500mL of isopropanol was added, the mixture was stirred and heated to 70 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-boscalid 138.62g, the yield is 91.8%, and the HPLC purity is 99%.
Example 7 preparation of S-configuration vitronectin by the method of the invention
212.0g of sodium carbonate (2.0 mol) are mixed with H 2 O (1.2L) was added to a 2L reaction flask, placed in an ice bath, stirred to dissolve, 150.13g D-xylose (1.0 mol) was added, and stirring was continued until dissolved. At room temperature, 150.13g acetylacetone (1.5 mol) is added, the internal temperature is raised to 70 ℃, and TCL is monitored in real time until the D-xylose reaction is complete. After the reaction is finished, cooling to room temperature, and adjusting the pH value to 4-5 by using hydrochloric acid. Ethyl acetate extraction (300ml x 3 times) collected the aqueous phase. The solvent was removed by rotary evaporation, followed by drying of mL with ethanol (450 x 3 times) to remove residual water. Adding 750mL of ethanol for dissolving, filtering undissolved substances, and removing the solvent by rotary evaporation to obtain 150.12g of crude product beta-xylopyranoside with the yield of about 79.1%.
150.0g of crude beta-xylopyranoside (0.79 mol), 5.14g of ruthenium catalyst cat.C (7.9 mmol) and 1.77g of potassium hydroxide (31.6 mmol) were added to a reaction flask, nitrogen was replaced three times, 300mL of isopropanol and 300mL of water were added, the mixture was stirred and heated to 70 ℃ and TLC was followed until the reaction material was completely consumed. Subsequently, hydrochloric acid was added to adjust the pH to 7, and the solvent was removed by rotary evaporation. Adding 200mL of methanol again, heating to 50 ℃ to dissolve until the solid is basically dissolved, filtering while the solution is hot, standing the filtrate, cooling to room temperature, crystallizing, filtering, washing, and drying in vacuum to obtain the product S-vitriol 132.68g, the yield is 87.9%, and the HPLC purity is 99%.
The nuclear magnetic data of the product S-vitreochrome prepared by the invention: 1 H NMR(400MHz,D 2 O)δ(ppm)3.95–3.85(m,1H),3.84–3.80(m,1H)，3.50–3.44(m,1H),3.30-3.05(m,4H),1.84–1.78(m,1H),1.59-1.51(m,1H),1.09(d,J＝8.1Hz,3H)。
in conclusion, the invention provides a synthesis method of stereospecific hydroxypropyl tetrahydropyran triol (vitronectin), which adopts a specific chiral catalyst for regulation and control, utilizes a metal-catalyzed hydrogen transfer reaction to realize efficient and stereospecific reduction of beta-acetone xyloside, and obtains the specific S-configuration vitronectin. The synthetic method has the advantages of simple operation steps, mild reaction conditions, easy post-treatment, good safety and the like, and the prepared S-shaped vitreous color factor has high yield and high purity and has the potential of industrial production of the S-shaped vitreous color factor.
Claims (10)
1. A synthetic method of stereospecific hydroxypropyl tetrahydropyrane triol is characterized in that: it comprises the following steps:
(1) Taking compound 1D-xylose as a raw material, and carrying out Knoevenagel condensation reaction with acetylacetone in a water phase to prepare compound 2 beta-acetone xyloside;
(2) In an isopropanol system, promoting hydrogen transfer reaction of beta-xyloside acetone by a catalyst under an alkaline condition to realize reduction of the beta-xyloside acetone to obtain a compound 3S-configuration vitreochrome.
2. The method of synthesis according to claim 1, characterized in that: in the step (1), the water phase is an alkali water solution; preferably, the concentration of the alkali is 1 to 5mol/L.
3. The method of synthesis according to claim 2, characterized in that: in the step (1), the molar ratio of the D-xylose to the acetylacetone is 1:1.0 to 4.0; preferably 1:1.0 to 2.0;
and/or, in the step (1), the molar ratio of the D-xylose to the alkali is 1:1.0 to 4.0; preferably 1:1.0 to 3.0.
4. A synthesis method according to claim 2 or 3, characterized in that: in the step (1), the alkali is any one or more of sodium carbonate, sodium hydroxide, potassium hydroxide and sodium bicarbonate.
5. The method of synthesis according to claim 1, characterized in that: in the step (2), the isopropanol system is an isopropanol solvent or a mixed solvent containing isopropanol.
6. The method of synthesis according to claim 5, characterized in that: in the step (2), the volume ratio of the isopropanol to other solvents is 1:0.1 to 10;
preferably, the other solvent is any one or more of water, isopropanol, methanol, ethanol and tetrahydrofuran.
7. The method of synthesis according to claim 1, characterized in that: in the step (2), the mol ratio of the beta-acetone xyloside to the catalyst to the alkali is 1:0.01 to 0.1:0.01 to 0.2; preferably 1:0.01 to 0.05:0.01 to 0.1.
8. The method of synthesis according to claim 1, characterized in that: in the step (2), the catalyst is one or more of Noyori (S, S) -ruthenium catalyst.
9. The method of synthesis according to claim 8, characterized in that: in the step (2), the catalyst is one or more of Cat.A, cat.B and Cat.C:
10. the method of synthesis according to claim 1, characterized in that: in the step (1), the temperature of the Knoevenagel condensation reaction is 0-90 ℃; the reaction temperature is preferably 30-70 ℃;
and/or, in the step (2), the temperature of the hydrogen transfer reaction is 0-120 ℃; the reaction temperature is preferably 25 to 60 ℃.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116253707A (en) * | 2023-05-15 | 2023-06-13 | 山东梅奥华卫科技有限公司 | Synthesis method of high-purity glass color factor |
| CN117050045A (en) * | 2023-10-10 | 2023-11-14 | 长沙创新药物工业技术研究院有限公司 | Synthesis method of S-configuration hydroxypropyl tetrahydropyran triol |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116253707A (en) * | 2023-05-15 | 2023-06-13 | 山东梅奥华卫科技有限公司 | Synthesis method of high-purity glass color factor |
| CN117050045A (en) * | 2023-10-10 | 2023-11-14 | 长沙创新药物工业技术研究院有限公司 | Synthesis method of S-configuration hydroxypropyl tetrahydropyran triol |
| CN117050045B (en) * | 2023-10-10 | 2023-12-22 | 长沙创新药物工业技术研究院有限公司 | Synthesis method of S-configuration hydroxypropyl tetrahydropyran triol |
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