CN105218600A - A kind of synthetic method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate - Google Patents
A kind of synthetic method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate Download PDFInfo
- Publication number
- CN105218600A CN105218600A CN201510669042.9A CN201510669042A CN105218600A CN 105218600 A CN105218600 A CN 105218600A CN 201510669042 A CN201510669042 A CN 201510669042A CN 105218600 A CN105218600 A CN 105218600A
- Authority
- CN
- China
- Prior art keywords
- mannopyranose
- ethanoyl
- acetyl
- mannose
- synthesis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Abstract
The invention discloses a kind of 2; 3; 4; the synthetic method of 6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate; the method comprises D-MANNOSE and pyridylacetic acid(HPAC) acid anhydride through being uniformly mixed; be that catalyzer synthesizes full acidylate mannopyranose with DMAP; then by full acidylate mannopyranose in organic solvent selectivity take off C1 position ethanoyl and obtain 2; 3,4,6-tetra--O-ethanoyl-D-MANNOSE; last reaction obtained 2 under base catalysis; 3,4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines.Method simple and effective of the present invention, product yield is high.
Description
Technical field
The invention belongs to chemosynthesis technical field, relate in particular to a kind of preparation method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate.
Background technology
Seminose, unique for saccharic nutrient substance clinically at present, be distributed widely in body fluid and tissue, it is directly utilized synthesis glycoprotein, participates in immunomodulatory.Numerous disease causes just because of the ferment lacked in seminose saccharification.Its physiological effect in human body is as follows: 1) immunity moderation system 2) Macrophage Surface has 4 kinds of susceptors can capture antigen, have mannose component 3) increase wound healing 4) anti-inflammation effect 5) and Tumor suppression growth with transfer, increase cancer survival rate 6) some bacteriological infection can be avoided, as urinary tract infection.
In chemical synthesis, Koenigs ?the stereoselective syntheses glucosides of Knorr method to be a kind of conventional silver salt and mercury salt the be classics of catalyzer, but there is the poor stability of glycosyl donor halogeno-sugar, not easily preserve, used catalyst is heavy metallic salt, expensive, the problems such as environmental pollution is serious.
2; 3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate has the plurality of advantages such as Stability Analysis of Structures stereoselectivity is good under active good low temperature; can be used for synthesis sulphur glycosides, oxygen glycosides, carbon glycosides and nitrogen glycosides etc., in the synthesis such as mannosans and glycosyl albumen, have important effect.Therefore, research 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate, as the important intermediate of synthesis sugar esters compounds, has become the another much-talked-about topic in life science field.
Summary of the invention
The object of the invention is to solve in prior art and be inadequate; a kind of synthesis 2 is provided; 3; 4; the novel method of 6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines; solve the poor stability of glycosyl donor halogeno-sugar, not easily preserve, not easily obtain the problem with the glycosylation reagent of potential pharmaceutical use.
Specifically, the present invention is achieved through the following technical solutions.
A kind of 2; 3; 4; the synthetic method of 6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate; it is characterized in that; D-MANNOSE and pyridylacetic acid(HPAC) acid anhydride, through being uniformly mixed, are that catalyzer synthesizes full acidylate mannopyranose with DMAP, then by full acidylate mannopyranose in organic solvent selectivity take off C1 position ethanoyl and obtain 2; 3; 4,6-tetra--O-ethanoyl-D-MANNOSE, finally reaction obtained 2 under base catalysis; 3; 4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines, its synthesis step comprises:
The synthesis of (1) five acetyl mannopyranose
At 0 DEG C, D-MANNOSE is dissolved in pyridine, slowly adds diacetyl oxide, and mixture is placed in 0 DEG C of ice-water bath and stirs 0.5 ~ 1h, adds the DMAP of catalytic amount, at room temperature reacts 6h, obtain five acetyl mannopyranose solution;
The synthesis of (2) 2,3,4,6-tetra--O-ethanoyl-D-MANNOSEs
Five acetyl mannopyranoses are mixed with the mass volume ratio of tetrahydrofuran (THF) by 1g:15-20mL, benzylamine is dripped wherein under the condition of ice bath, under ice bath, 0.5 ~ 1h is stirred after dropwising, then react 30h at ambient temperature, reaction terminates rear underpressure distillation removing tetrahydrofuran (THF), and residue methylene dichloride dissolves, use 1M hydrochloric acid soln and water washing successively, drying, filtering and concentrating, obtains water white transparency viscous product;
The synthesis of (3) 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate
By 2; 3; 4,6-tetra--O-ethanoyl-D-MANNOSE mixes with the mass volume ratio of dry methylene chloride by 1g:10-15mL, adds Trichloroacetonitrile subsequently and stirs 10min; the basic catalyst adding catalytic amount stirs 30h; reaction terminates the water of rear mixture 50mL and saturated aqueous common salt washs successively, dry, filters; vacuum concentration, obtains colorless viscous product.
Preferably, in step (1), the mol ratio of D-MANNOSE and diacetyl oxide is 1:10-20.
Preferably, the solvent of full acetylated reaction is pyridine, and the mol ratio of pyridine and D-MANNOSE is 25-45:1.
Preferably, after five acetyl mannopyranose synthesis acquisition five acetyl mannopyranose solution of step (1), also comprise the treatment step to five acetyl mannopyranose solution, the treating step comprises: this five acetyl mannopyranose solution is poured in the frozen water of rapid stirring, after stirring 30min, be extracted with ethyl acetate, merge organic phase, washing, dry, vacuum concentration, obtains colorless viscous shape product.
Further, after merging organic phase, the methylbenzene azeotropic comprised the organic phase of merging is dry further takes moieties pyridine out of, washs successively subsequently with copper/saturated copper sulphate solution, saturated aqueous common salt, saturated sodium bicarbonate solution.
Further, the colorless viscous product obtained also comprises following further process: dissolve with anhydrous diethyl ether, then at refrigerator overnight freezing and crystallizing, obtain white five acetyl mannopyranoses.
Preferably, in step (2), the mol ratio of five acetyl mannopyranoses and benzylamine is 1:1.19-1.25.
Preferably, in step (3), the mol ratio of 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE and Trichloroacetonitrile is 1:1.5-2.0.
Preferably, in step (3), basic catalyst used is cesium carbonate.
Compared with prior art the present invention has following beneficial effect:
The method that the present invention synthesizes 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate overcomes some technological deficiencies existed in prior art, and method simple and effective of the present invention, product yield is high.
Embodiment
The object of the present invention is to provide a kind of synthesis 2 newly; 3; 4; the method of 6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines; comprise D-MANNOSE and pyridylacetic acid(HPAC) acid anhydride through being uniformly mixed; with DMAP (DMAP) for catalyzer synthesizes full acidylate mannopyranose; then by full acidylate mannopyranose in organic solvent selectivity take off C1 position ethanoyl and obtain 2; 3,4,6-tetra--O-ethanoyl-D-MANNOSE; last reaction obtained 2 under base catalysis; 3,4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines.
Specifically, the step of the synthetic method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines is as follows:
(1) five acetyl mannopyranoses are synthesized
At 0 DEG C, D-MANNOSE is dissolved in pyridine, slowly adds diacetyl oxide, and mixture is placed in 0 DEG C of ice-water bath and stirs 0.5 ~ 1h, adds the DMAP (DMAP) of catalytic amount, at room temperature reacts 6h, obtain five acetyl mannopyranose solution;
(2) 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE is synthesized
Five acetyl mannopyranoses are mixed by 1g:15-20mL mass volume ratio with tetrahydrofuran (THF), benzylamine is dripped wherein under the condition of ice bath, under ice bath, 0.5 ~ 1h is stirred after dropwising, then react 30h under room temperature condition, reaction terminates rear underpressure distillation removing tetrahydrofuran (THF), and residue methylene dichloride dissolves, use 1M hydrochloric acid soln and water washing successively, drying, filtering and concentrating, obtains water white transparency viscous product;
(3) 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate is synthesized
By 2; 3; 4; 6-tetra--O-ethanoyl-D-MANNOSE mixes by 1g:10-15mL mass volume ratio with dry methylene chloride, adds Trichloroacetonitrile subsequently and stirs 10min, and the basic catalyst adding catalytic amount stirs 30h; reaction terminates the water of rear mixture 50mL and saturated aqueous common salt washs successively; drying, filtering vacuum concentrates, and obtains colorless viscous product.
A preferred embodiment of the invention, the mol ratio of D-MANNOSE and diacetyl oxide is 1:10-20.
A preferred embodiment of the invention, the solvent of full acetylated reaction is pyridine, and the mol ratio of pyridine and D-MANNOSE is 25-45:1.
A preferred embodiment of the invention, also five obtained acetyl mannopyranose solution are processed further, treatment step comprises to be poured in the frozen water of rapid stirring by five obtained acetyl mannopyranose solution, after stirring 30min, be extracted with ethyl acetate, merge organic phase, washing, drying, vacuum concentration, obtains colorless viscous shape product.
According to one of the present invention more preferably embodiment, after above-described merging organic phase step, the methylbenzene azeotropic that the organic phase of merging is dry takes moieties pyridine out of, washs successively subsequently with copper/saturated copper sulphate solution, saturated aqueous common salt, saturated sodium bicarbonate solution.
According to another kind of the present invention more preferably embodiment, the colorless viscous product anhydrous diethyl ether obtained by the above dissolves, and then at refrigerator overnight freezing and crystallizing, obtains white five acetyl mannopyranoses.
A preferred embodiment of the invention, the mol ratio of five acetyl mannopyranoses and benzylamine is 1:1.19-1.25.
A preferred embodiment of the invention, the mol ratio of 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE and Trichloroacetonitrile is 1:1.5-2.0.
A preferred embodiment of the invention, basic catalyst used in step (3) is cesium carbonate.
In more detail the present invention will be described below.
The present invention relates to a kind of synthetic method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines.
The step of the method is as follows:
The synthesis of (1) five acetyl mannopyranose
At 0 DEG C, D-MANNOSE is dissolved in pyridine, slowly adds diacetyl oxide, and mixture is placed in 0 DEG C of ice-water bath and stirs 0.5 ~ 1h, adds the DMAP (DMAP) of catalytic amount, at room temperature reacts 6h, obtain five acetyl mannopyranose solution.
D-MANNOSE is current commercially obtainable product.Diacetyl oxide is also referred to as acetic anhydride, is also current commercially obtainable product.
Preferably, the mol ratio of D-MANNOSE and diacetyl oxide is 1:10-20.
More preferably, the mol ratio of D-MANNOSE and diacetyl oxide is 1:12.
After full acylation reaction terminates, solution is poured in the frozen water of rapid stirring, after stirring 30min, be extracted with ethyl acetate, merge organic phase.
After merging organic phase, take moieties pyridine out of with the methylbenzene azeotropic of drying, wash successively with copper/saturated copper sulphate solution, saturated aqueous common salt, saturated sodium bicarbonate solution subsequently.
After extraction, colorless viscous product anhydrous diethyl ether dissolves, and then at refrigerator overnight freezing and crystallizing, obtains white five acetyl mannopyranoses.
The five acetyl mannopyranoses that this step obtains can adopt nmr analysis method, identify product.
The five acetyl mannopyranoses that this step obtains treatedly can not be directly used in the reaction of subsequent step.
The synthesis of (2) 2,3,4,6-tetra--O-ethanoyl-D-MANNOSEs
The five acetyl mannopyranoses above step obtained mix by 1g:15-20mL mass volume ratio with tetrahydrofuran (THF), benzylamine is dripped wherein under the condition of ice bath, under ice bath, 0.5 ~ 1h is stirred after dropwising, then react 30h under room temperature condition, reaction terminates rear underpressure distillation removing tetrahydrofuran (THF), and residue methylene dichloride dissolves, use 1M hydrochloric acid soln and water washing successively, drying, filtering and concentrating, obtains water white transparency viscous product.
Preferably, the mol ratio of five acetyl mannopyranoses and benzylamine is 1:1.19-1.25.
More preferably, the mol ratio of five acetyl mannopyranoses and benzylamine is 1:1.23.
The synthesis of (3) 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate
To obtain above 2; 3; 4; 6-tetra--O-ethanoyl-D-MANNOSE mixes by 1g:10-15mL mass volume ratio with dry methylene chloride, adds Trichloroacetonitrile subsequently and stirs 10min, and the basic catalyst adding catalytic amount stirs 30h; reaction terminates the water of rear mixture 50mL and saturated aqueous common salt washs successively; drying, filtering vacuum concentrates, and obtains colorless viscous product.
Preferably, the mol ratio of 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE and Trichloroacetonitrile is 1:1.5-2.0.
More preferably, the mol ratio of 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE and Trichloroacetonitrile is 1:1.74.
Preferably, basic catalyst is cesium carbonate.
Further by specific embodiment, the present invention is described below, but the present invention is not merely defined in these embodiments.
embodiment 1
(1) five acetyl mannopyranoses are synthesized
At 0 DEG C, in the round-bottomed flask of 100mL, be dissolved in by 3gD-seminose in 33mL purifying pyridine, slowly add the diacetyl oxide of 31.5mL drying, mixture stirs 1h at 0 DEG C, adds the DMAP (DMAP) of catalytic amount, at room temperature reacts 6h.After reaction terminates, mixture is poured in the frozen water of rapid stirring, after stirring 30min, use 100mL extraction into ethyl acetate, concentrated organic phase, takes moieties pyridine out of with the methylbenzene azeotropic of drying, subsequently by the organic phase after copper/saturated copper sulphate solution, saturated aqueous common salt, saturated sodium bicarbonate solution successively washing through anhydrous sodium sulfate drying, filtering and concentrating, from obtaining colorless viscous shape product, productive rate is 96%.
(2) 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE is synthesized
In the round-bottomed flask of 100mL, five acetyl mannopyranoses (1.6g) are dissolved in 30mL tetrahydrofuran (THF) (THF), drip 0.55mL benzylamine wherein, stir 30min after dropwising under ice bath, then react 30h under room temperature condition under the condition of ice bath.Reaction terminates rear underpressure distillation removing tetrahydrofuran (THF), and residue 30mL methylene dichloride dissolves, and uses 1M hydrochloric acid soln and water washing successively, organic phase anhydrous magnesium sulfate drying after having washed, filtering and concentrating organic phase, obtains water white transparency viscous product, and productive rate is 88%.
(3) 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate is synthesized
In the round-bottomed flask of 100mL, 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE (3g) is dissolved in 30mL dry methylene chloride, and the Trichloroacetonitrile adding 1.5mL subsequently stirs 10min, and the cesium carbonate adding catalytic amount stirs 30h.Reaction terminates the water of rear mixture 50mL and saturated aqueous common salt washs successively, the organic phase anhydrous sodium sulfate drying after washing, and filtering vacuum concentrates, and obtain white solid, productive rate is 90%.
1HNMR(400MHz,CDCl3):δ8.78(s,1H;NH),6.27(d,J=5.3Hz,1H;H-1),5.46–5.47(d,J=5.3Hz,1H;H-4),5.40(dd,J=5.3and18Hz,1H;H-3),5.38-5.39(dd,J=5.5and18Hz,1H;H-2),4.25–4.28(t,J=10.7Hz,1H;H-5),4.17–4.19(m,1H;H-6a),4.09–4.14(m,1H;H-6b),2.19(s,3H;OAc),2.07(s,3H;OAc),2.06(s,3H;OAc),2.00(s,3H;OAc)。
application Example 1
P-methoxyphenyl-2,3, the synthesis of 4,6-tetra--O-ethanoyl-D-MANNOSE glycosides
8.00g(16.29mmol is added in 100mL round-bottomed flask) 2; 3; 4; 6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate, 6.07g (48.88mmol) p methoxy phenol and 50mLCH2Cl2; after stirring and dissolving; under condition of ice bath; drip 2.10mL (16.29mmol) boron trifluoride ether solution; after being placed in 0 DEG C of ice bath cooling and stirring 4h; TLC monitoring reacts completely, decompress filter, and filtrate concentrates; column chromatography for separation obtains white solid 5.69g, yield 76.9%.105~107℃。
In conjunction with specific embodiments embodiments of the present invention are described in detail above, but the invention is not restricted to above-mentioned embodiment, in the ken that art those of ordinary skill possesses, can also make a variety of changes under the prerequisite not departing from present inventive concept.
Claims (9)
1. one kind 2; 3; 4; the synthetic method of 6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate; it is characterized in that; D-MANNOSE and pyridylacetic acid(HPAC) acid anhydride, through being uniformly mixed, are that catalyzer synthesizes full acidylate mannopyranose with DMAP, then by full acidylate mannopyranose in organic solvent selectivity take off C1 position ethanoyl and obtain 2; 3; 4,6-tetra--O-ethanoyl-D-MANNOSE, finally reaction obtained 2 under base catalysis; 3; 4,6-O-ethanoyl-α-D-mannopyranose tribromo-acetyl imines, its synthesis step comprises:
The synthesis of (1) five acetyl mannopyranose
At 0 DEG C, D-MANNOSE is dissolved in pyridine, slowly adds diacetyl oxide, and mixture is placed in 0 DEG C of ice-water bath and stirs 0.5 ~ 1h, adds the DMAP of catalytic amount, at room temperature reacts 6h, obtain five acetyl mannopyranose solution;
The synthesis of (2) 2,3,4,6-tetra--O-ethanoyl-D-MANNOSEs
Five acetyl mannopyranoses are mixed with the mass volume ratio of tetrahydrofuran (THF) by 1g:15-20mL, benzylamine is dripped wherein under the condition of ice bath, under ice bath, 0.5 ~ 1h is stirred after dropwising, then react 30h at ambient temperature, reaction terminates rear underpressure distillation removing tetrahydrofuran (THF), and residue methylene dichloride dissolves, use 1M hydrochloric acid soln and water washing successively, drying, filtering and concentrating, obtains water white transparency viscous product;
The synthesis of (3) 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate
By 2; 3; 4,6-tetra--O-ethanoyl-D-MANNOSE mixes with the mass volume ratio of dry methylene chloride by 1g:10-15mL, adds Trichloroacetonitrile subsequently and stirs 10min; the basic catalyst adding catalytic amount stirs 30h; reaction terminates the water of rear mixture 50mL and saturated aqueous common salt washs successively, dry, filters; vacuum concentration, obtains colorless viscous product.
2. method according to claim 1, is characterized in that, in step (1), the mol ratio of D-MANNOSE and diacetyl oxide is 1:10-20.
3. method according to claim 1, is characterized in that, the solvent of full acetylated reaction is pyridine, and the mol ratio of pyridine and D-MANNOSE is 25-45:1.
4. method according to claim 1, it is characterized in that, after five acetyl mannopyranose synthesis acquisition five acetyl mannopyranose solution of step (1), also comprise the treatment step to five acetyl mannopyranose solution, the treating step comprises: this five acetyl mannopyranose solution is poured in the frozen water of rapid stirring, after stirring 30min, be extracted with ethyl acetate, merge organic phase, washing, drying, vacuum concentration, obtains colorless viscous shape product.
5. method according to claim 4, it is characterized in that, after merging organic phase, the methylbenzene azeotropic comprised the organic phase of merging is dry further takes moieties pyridine out of, washs successively subsequently with copper/saturated copper sulphate solution, saturated aqueous common salt, saturated sodium bicarbonate solution.
6. method according to claim 4, is characterized in that, also further comprising the steps: dissolved by the colorless viscous product anhydrous diethyl ether obtained, and then at refrigerator overnight freezing and crystallizing, obtains white five acetyl mannopyranoses.
7. method according to claim 1, is characterized in that, in step (2), the mol ratio of five acetyl mannopyranoses and benzylamine is 1:1.19-1.25.
8. method according to claim 1, is characterized in that, in step (3), the mol ratio of 2,3,4,6-tetra--O-ethanoyl-D-MANNOSE and Trichloroacetonitrile is 1:1.5-2.0.
9. method according to claim 1, is characterized in that, in step (3), basic catalyst used is cesium carbonate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510669042.9A CN105218600B (en) | 2015-10-13 | 2015-10-13 | A kind of synthetic method of 2,3,4,6-O- acetyl group-α-D- mannopyranose tri- chloroacetimidates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510669042.9A CN105218600B (en) | 2015-10-13 | 2015-10-13 | A kind of synthetic method of 2,3,4,6-O- acetyl group-α-D- mannopyranose tri- chloroacetimidates |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN105218600A true CN105218600A (en) | 2016-01-06 |
| CN105218600B CN105218600B (en) | 2018-06-08 |
Family
ID=54987929
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201510669042.9A Expired - Fee Related CN105218600B (en) | 2015-10-13 | 2015-10-13 | A kind of synthetic method of 2,3,4,6-O- acetyl group-α-D- mannopyranose tri- chloroacetimidates |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN105218600B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113861246A (en) * | 2021-11-02 | 2021-12-31 | 中山大学 | Stereoselective synthesis method of beta-D-arabinofuranoside bond |
-
2015
- 2015-10-13 CN CN201510669042.9A patent/CN105218600B/en not_active Expired - Fee Related
Non-Patent Citations (3)
| Title |
|---|
| HUSSEIN AL-MUGHAID ET AL.: "《Unique tetrameric and hexameric mannoside clusters prepared by click chemistry》", 《CARBOHYDRATE RESEARCH》 * |
| TIHOMIR TOMASIC ET AL.: "《Monovalent mannose-based DC-SIGN antagonists: Targeting the hydrophobic groove of the receptor》", 《EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY》 * |
| YONGSHUN HUANG ET AL.: "《Synthesis and Anticoagulant Activity of Polyureas Containing Sulfated Carbohydrates》", 《BIOMACROMOLECULES》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113861246A (en) * | 2021-11-02 | 2021-12-31 | 中山大学 | Stereoselective synthesis method of beta-D-arabinofuranoside bond |
| CN113861246B (en) * | 2021-11-02 | 2024-01-05 | 中山大学 | Stereoselective synthesis method of beta-D-arabinofuranoside bond |
Also Published As
| Publication number | Publication date |
|---|---|
| CN105218600B (en) | 2018-06-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN101671375B (en) | Bromotetraacetylglucose, synthetic method and use thereof | |
| CN105218611B (en) | Preparation method of 20th carbon hydroxyl dehydrated ginseng rare saponin and aglycone | |
| CN105461772A (en) | Trifluridine intermediate and preparation method of trifluridine | |
| CN106256824A (en) | A kind of preparation method of high-purity De Lasha star meglumine salt | |
| CN113549042A (en) | Preparation method of dapagliflozin | |
| CN108473524A (en) | A kind of Preparation Method And Their Intermediate of Tulathromycin | |
| CN101735288A (en) | Method for complete acetylization of saccharides in presence of solid acid catalyst | |
| CN104744540A (en) | Preparation method for regadenoson | |
| CN105218600A (en) | A kind of synthetic method of 2,3,4,6-O-ethanoyl-α-D-mannopyranose tri-chloroacetimidate | |
| CN107286207B (en) | Synthesis method of gentiobiose | |
| CN103833714A (en) | Semi-synthesis method of luteolin and galuteolin as well as luteolin rutinoside | |
| CN108191925A (en) | The industrial manufacturing process of gemcitabine key intermediate sulfonation sugar | |
| CN103601766B (en) | Fondaparinux sodium pentasaccharide intermediate and preparation method thereof | |
| CN107629095A (en) | The full acetyl sugar end position selectivity deprotection method of trifluoromethanesulfonic acid hafnium catalysis | |
| CN108610386A (en) | A kind of preparation method of substituted benzyl or substituted-phenyl β-D- hexuronic acid glucosides | |
| CN109336856A (en) | A kind of preparation method of the bromo- D- glucal of 6- | |
| CN104432110A (en) | Preparation method of sulfated apple water-soluble dietary fiber | |
| CN103833796B (en) | Prepare the method for angustose | |
| CN108912239A (en) | A kind of synthetic method of poly- seven sugar in 3,6 branching Portugals | |
| CN113072598A (en) | Method for continuously preparing emamectin benzoate and intermediate thereof | |
| CN100564340C (en) | (2E, 4E)-preparation method of 2-methyl-6-oxo-2 | |
| CN104650160A (en) | Novel synthesis method of capecitabine key intermediate 1,2,3-O-triacetyl-5-deoxy-D-ribose | |
| CN107141322B (en) | Method for chemically synthesizing tetraacetyl geraniol glycoside by using immobilized catalyst | |
| CN105198940B (en) | A kind of glucurone preparation process | |
| CN104098618A (en) | Intermediate of fondaparinux sodium and preparation method for intermediate and fondaparinux sodium |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CF01 | Termination of patent right due to non-payment of annual fee |
Granted publication date: 20180608 Termination date: 20211013 |
|
| CF01 | Termination of patent right due to non-payment of annual fee |