CN105646612A - Method for synthesizing alpha-aryl thioglycoside - Google Patents

Method for synthesizing alpha-aryl thioglycoside Download PDF

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CN105646612A
CN105646612A CN201610122381.XA CN201610122381A CN105646612A CN 105646612 A CN105646612 A CN 105646612A CN 201610122381 A CN201610122381 A CN 201610122381A CN 105646612 A CN105646612 A CN 105646612A
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sulfur glycosides
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CN105646612B (en
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朱向明
王兴娣
杨晓鹏
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Zhejiang Normal University CJNU
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    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/20—Carbocyclic rings
    • C07H15/203—Monocyclic carbocyclic rings other than cyclohexane rings; Bicyclic carbocyclic ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives

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Abstract

The invention provides a method for synthesizing alpha-aryl thioglycoside. The method includes steps that alpha-glycosyl thiol is used as a substrate in solvents N, N-dimethylformamide, tetrabutylammonium bromide is used as a ligand in the solvents, and the substrate and the ligand react to aryl iodide under the catalytic effects of copper iodide to obtain the alpha-aryl thioglycoside. Aryl halide directly reacts to thiophenol or thiol at one step under the catalytic effects of copper reagents to obtain coupled products, and the configuration of the original thiol can keep unchanged in procedures. The method has the advantages of mild conditions, high yield, inexpensive required reagents and the like.

Description

A kind of method synthesizing alpha-aromatic sulfur glycosides
Technical field
The invention belongs to the carbohydrate chemistry synthesis field in organic chemistry, particularly to a kind of method preparing alpha-aromatic sulfur glycosides.
Background technology
Sulfur glycosides is widely used in oligosaccharide synthesizes, and is due to sulfur glycosides donor good stability on the one hand, and can be used as donor also can as provisional protection base, it is also possible to transform into other donor; On the other hand the activity of sulfur glycosides donor can have the protection base (especially 2-is protection base) of the hydroxyl on sugared ring, protect base, the configuration of sulfur glycosides and the reaction dissolvent etc. of sulphur atom regulate and control; therefore; sulfur glycosides can be applicable to " Armed-disarmed " strategy, it is achieved the orientation between different sulfur glycosides is glycosylation. Therefore the sulfur glycosides efficiently synthesizing various configuration just becomes extremely important,
The synthesis of at present-aryl sulfur glycosides mostly adopts end group center S-nucleophilic displacement, has both adopted ��-halogeno-sugar and thiophenol generation nucleophilic substitution. And ��-halogeno-sugar reactivity is higher, very difficult exist at normal temperatures, brings difficulty for synthesis on a large scale. So up to the present, but without the method for a kind of efficient preparation-aryl sulfur glycosides.
Summary of the invention
In order to overcome the defect existed in prior art, the invention provides a kind of synthetic method preparing alpha-aromatic sulfur glycosides. The method, with alpha-glycosyl mercaptan for substrate, then passes through the Ullmann reaction of CuI catalysis, can efficiently prepare-aryl sulfur glycosides. The present invention by aryl halide under cupferron catalysis directly and thiophenol or mercaptan single step reaction obtain the product of coupling, and the retention of configuration of former mercaptan can be kept in the process constant. The method has mild condition, productivity is high and uses the advantages such as reagent is cheap.
A kind of method synthesizing alpha-aromatic sulfur glycosides, it is characterised in that comprise the following steps: at solvent N, in dinethylformamide, with alpha-glycosyl mercaptan for substrate, with tetrabutyl ammonium bromide for part, under Hydro-Giene (Water Science). catalysis, react to obtain alpha-aromatic sulfur glycosides with iodo aromatic hydrocarbon; Reaction equation is as follows:
Further, reaction temperature is 80 DEG C.
Reaction system has been additionally added potassium phosphate.
The method of synthesis alpha-aromatic sulfur glycosides, concrete technology comprises the steps: to be placed in two neck round-bottomed flasks by Hydro-Giene (Water Science)., tetrabutyl ammonium bromide, potassium phosphate, iodo aromatic hydrocarbon, evacuation, changes nitrogen three times; Being dissolved in N in nitrogen atmosphere, the alpha-glycosyl thiol solution in N-dimethylformamide solvent adds in round-bottomed flask; Being placed in oil bath by round-bottomed flask, be warming up to 80 DEG C of reaction 4h, reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds saturated aqueous common salt and ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask;Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains alpha-aromatic sulfur glycosides.
In said method, iodo aromatic hydrocarbon, if liquid, is dissolved in DMF solvent by iodo aromatic hydrocarbon together with alpha-glycosyl mercaptan.
Compared with the conventional method, by the present invention in that and prepare alpha-aromatic sulfur glycosides with Cul catalysis alpha-glycosyl mercaptan and iodo aromatic hydrocarbon reaction. It is advantageous that:
(1) this method reaction condition is gentle, productivity is high, product is easily separated, simple to operate.
(2) this method agents useful for same is cheap especially, overcomes the shortcoming using expensive reagents in traditional method.
(3) this method by aryl halide under Hydro-Giene (Water Science). catalysis directly and thiophenol or mercaptan single step reaction obtain the product of coupling, and the retention of configuration of former mercaptan can be kept in the process constant.
Detailed description of the invention
The preparation of embodiment 1:6-O-hydroxyl-2,3,4-three-O-benzyl-1-S-phenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; evacuation; inflated with nitrogen three times; then it is dissolved in 0.47g (1mmol) the alpha-glycosyl mercaptan glucose in DMF solvent with disposable syringe under nitrogen protection and 0.17g (0.8mmol) iodobenzene solution is injected in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 4h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.36g, and productivity is 80%.1HNMR(600MHz,CDCl3) �� 7.48 7.28 (m, 22H), 5.57 (d, J=5.4Hz, 1H), 5.01 (d, J=10.8Hz, 1H), 4.89 (d, J=11.0Hz, 1H), 4.83 (d, J=10.8Hz, 1H), 4.77 (d, J=11.6Hz, 1H), 4.70 (d, J=11.6Hz, 2H), 4.65 (d, J=11.0Hz, 1H), 4.23 4.18 (m, 1H), 3.93 (t, J=9.2Hz, 1H), 3.85 (dd, J=9.6,5.4Hz, 1H), 3.70 (dd, J=13.7,8.1Hz, 3H), 3.57 (dd, J=9.9,9.0Hz, 1H);13CNMR(151MHz,CDCl3)��138.7,138.2,137.7,134.1, 132.1,129.1,128.6,128.6,128.6,128.5,128.2,128.2,128.1,128.1,128.0,127.8,127.5,87.0,82.4,80.0,75.8,75.2,72.7,71.9,61.8��
The preparation of embodiment 2:6-O-hydroxyl-2,3,4-three-O-benzyl-1-S-p-methylphenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; 183mg (0.8mmol) 4-iodotoluene; evacuation; inflated with nitrogen three times; then 0.47g (1mmol) the alpha-glycosyl mercaptan injected glucose solutions being dissolved in DMF solvent with disposable syringe under nitrogen protection enters in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 4h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.38g, and productivity is 82%.1HNMR(600MHz,CDCl3) �� 7.45 7.38 (m, 2H), 7.38 7.27 (m, 16H), 7.11 (d, J=7.9Hz, 2H), 5.50 (d, J=5.4Hz, 1H), 5.00 (d, J=10.8Hz, 1H), 4.89 (d, J=11.0Hz, 1H), 4.83 (d, J=10.8Hz, 1H), 4.78 (d, J=11.7Hz, 1H), 4.70 (d, J=11.7Hz, 1H), 4.65 (d, J=11.0Hz, 1H), 4.32 4.18 (m, 1H), 3.93 (t, J=9.3Hz, 1H), 3.83 (dd, J=9.6, 5.4Hz, 1H), 3.78 3.64 (m, 2H), 3.55 (dd, J=9.8, 9.1Hz, 1H), 2.33 (s, 3H), 1.51 (t, J=6.3Hz, 1H),13CNMR(151MHz,CDCl3)��138.7,138.1,137.8,137.7,132.7,132.7,132.7,132.7,130.1,129.9,129.9,129.9,128.6,128.5,128.5,128.5,128.2,128.1,128.1,128.0,128.0,128.0,127.7,87.3,82.4,79.9,75.8,75.2,72.6,71.7��
The preparation of embodiment 3:6-O-hydroxyl-2,3,4-three-O-benzyl-1-S-p-nitrophenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 1177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; 209mg (0.8mmol) 4-iodotoluene; evacuation; inflated with nitrogen three times; then 0.47g (1mmol) the alpha-glycosyl mercaptan injected glucose solutions being dissolved in DMF solvent with disposable syringe under nitrogen protection enters in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 4h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.38g, and productivity is 77%.1HNMR(600MHz,CDCl3) �� 8.26 7.94 (m, 2H), 7.61 7.44 (m, 2H), 7.43 7.26 (m, 15H), 5.75 (d, J=4.5Hz, 1H), 4.99 (d, J=10.8Hz, 1H), 4.89 (d, J=11.0Hz, 1H), 4.84 (d, J=10.8Hz, 1H), 4.74 4.69 (m, 2H), 4.67 (d, J=11.0Hz, 1H), 4.02 (dt, J=10.0,3.0Hz, 1H), 3.95 3.88 (m, 2H), 3.72 (ddd, J=10.1,6.5,3.4Hz, 1H), 3.69 3.62 (m, 2H), 1.53 (d, J=5.2Hz, 1H);13CNMR(151MHz,CDCl3)��146.0,144.8,138.4,137.9,137.3,129.0,128.6,128.6,128.6,128.6,128.5,128.2,128.2,128.2,128.1,128.1,127.9,124.0,85.3,82.3,79.5,76.4,75.9,75.2,73.1,72.6,61.5��
The preparation of embodiment 4:6-O-acetyl group-2,3,4-three-O-benzyl-1-S-phenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; evacuation; inflated with nitrogen three times; then it is dissolved in N with disposable syringe under nitrogen protection; 0.51g (1mmol) 6-O-acetyl group-2 in N-dimethylformamide solvent; 3,4-tri--O-benzyl-1-mercaptan-alpha-D-glucose and 0.17g (0.8mmol) iodobenzene solution are injected in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 3h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.32g, and productivity is 67%.1HNMR(600MHz,CDCl3) �� 7.54 7.43 (m, 2H), 7.44 7.37 (m, 2H), 7.38 7.26 (m, 19H), 5.60 (d, J=5.3Hz, 1H), 5.03 (d, J=10.7Hz, 1H), 4.89 (d, J=10.8Hz, 1H), 4.82 (d, J=10.7Hz, 1H), 4.77 (d, J=11.7Hz, 1H), 4.70 (d, J=11.7Hz, 1H), 4.57 (d, J=10.8Hz, 1H), 4.46 4.35 (m, 1H), 4.29 (dd, J=11.9, 5.1Hz, 1H), 4.17 (dd, J=11.9, 1.9Hz, 1H), 3.97 3.91 (m, 1H), 3.88 (dd, J=9.6, 5.3Hz, 1H), 3.57 3.41 (m, 1H), 1.96 (s, 4H),13CNMR(151MHz,CDCl3)��170.7,138.5,137.8,137.6,134.0,131.9,129.0,128.6,128.6,128.5,128.4,128.2,128.2,128.1,128.1,128.0,127.8,127.4,86.8,82.5,79.7,75.9,75.2,72.6,69.6,63.1,20.8��
The preparation of embodiment 5:6-O-acetyl group-2,3,4-three-O-benzyl-1-S-p-methylphenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; 183mg (0.8mmol) 4-iodotoluene; evacuation; inflated with nitrogen three times; then it is dissolved in N with disposable syringe under nitrogen protection; 0.51g (1mmol) 6-O-acetyl group-2 in N-dimethylformamide solvent; 3,4-tri--O-benzyl-1-mercaptan-alpha-D-glucose solution is injected in round-bottomed flask.Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 3h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.34g, and productivity is 71%.1HNMR(600MHz,CDCl3) �� 7.40 (d, J=7.5Hz, 2H), 7.39 7.26 (m, 14H), 7.10 (d, J=8.0Hz, 2H), 5.53 (d, J=5.3Hz, 1H), 5.02 (d, J=10.7Hz, 1H), 4.89 (d, J=10.8Hz, 1H), 4.82 (d, J=10.7Hz, 1H), 4.78 (d, J=11.6Hz, 1H), 4.69 (d, J=11.7Hz, 1H), 4.57 (d, J=10.9Hz, 1H), 4.43 (dd, J=10.1, 4.9Hz, 1H), 4.29 (dd, J=11.9, 5.2Hz, 1H), 4.18 (d, J=11.9Hz, 1H), 3.94 (t, J=9.1Hz, 1H), 3.87 (dd, J=9.6, 5.4Hz, 1H), 3.50 (t, J=9.4Hz, 1H), 2.32 (s, 3H), 1.97 (s, 3H),13CNMR(151MHz,CDCl3)��170.7,149.9,138.5,137.8,137.6,137.6,132.5,130.0,129.8,128.6,128.5,128.5,128.2,128.2,128.1,128.0,128.0,127.8,87.2,82.4,79.8,75.9,75.1,72.5,69.5,63.2,21.2,20.8��
The preparation of embodiment 6:6-O-acetyl group-2,3,4-three-O-benzyl-1-S-p-nitrophenyl-alpha-D-glucose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; 209mg (0.8mmol) 4-iodotoluene; evacuation; inflated with nitrogen three times; then it is dissolved in N with disposable syringe under nitrogen protection; 0.51g (1mmol) 6-O-acetyl group-2 in N-dimethylformamide solvent; 3,4-tri--O-benzyl-1-mercaptan-alpha-D-glucose solution is injected in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 3h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.34g, and productivity is 68%.1HNMR(600MHz,CDCl3) �� 8.16 7.96 (m, 2H), 7.55 7.48 (m, 2H), 7.38 7.24 (m, 16H), 5.75 (d, J=4.8Hz, 1H), 5.00 (d, J=10.7Hz, 1H), 4.87 (d, J=10.8Hz, 1H), 4.82 (d, J=10.7Hz, 1H), 4.71 (s, 2H), 4.56 (d, J=10.8Hz, 1H), 4.28 4.18 (m, 2H), 4.15 (dd, J=11.7,1.5Hz, 1H), 3.99 3.80 (m, 2H), 3.52 (dd, J=9.6,8.4Hz, 1H), 1.92 (s, 3H);3CNMR(151MHz,CDCl3)��170.5,146.0,144.6,138.3,137.6,137.3,129.1,128.6,128.6,128.6,128.3,128.2,128.2,128.1,128.1,127.9,123.9,85.01,82.4,79.4,76.8,76.0,75.2,73.1,70.4,62.8��
The preparation of embodiment 7:6-O-hydroxyl-2,3,4-three-O-benzyl-1-S-p-nitrophenyl-��-D-galactose
Reaction equation is:
Under room temperature condition; 16mg (10mol%) Hydro-Giene (Water Science). is added in the two neck round-bottomed flasks of 50 milliliters; 177mg (0.8mmol) potassium phosphate; 42mg (0.13mmol) tetrabutyl ammonium bromide; 209mg (0.8mmol) 4-iodotoluene; evacuation; inflated with nitrogen three times; then 0.47g (1mmol) the alpha-glycosyl mercaptan galactose solution being dissolved in DMF solvent with disposable syringe under nitrogen protection is injected in round-bottomed flask. Round-bottomed flask is placed in oil bath, is warming up to 80 DEG C of reaction 4h, follows the tracks of the reaction mechanism mechanism of reaction by thin layer chromatography. Reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds appropriate saturated aqueous common salt, ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains product 0.38g, and productivity is 78%.1HNMR(600MHz,CDCl3) �� 8.13 7.99 (m, 2H), 7.55 7.43 (m, 2H), 7.42 7.24 (m, 16H), 5.91 (d, J=5.4Hz, 1H), 4.98 (d, J=11.5Hz, 1H), 4.89 (d, J=11.7Hz, 1H), 4.75 (dd, J=15.6, 11.6Hz, 3H), 4.65 (d, J=11.5Hz, 1H), 4.43 (dd, J=9.9, 5.4Hz, 1H), 4.07 (t, J=5.9Hz, 1H), 3.95 (d, J=1.7Hz, 1H), 3.82 (dd, J=10.0, 2.8Hz, 1H), 3.63 (dd, J=9.2, 6.3Hz, 1H), 3.50 (dd, J=11.8, 6.2Hz, 1H),13CNMR(151MHz,CDCl3)��145.8,145.1,138.3,137.9,137.7,128.9,128.6,128.6,128.6,128.6,128.6,128.5,128.2,128.1,128.1,128.0,127.9,127.7,123.9,85.7,79.4,76.1,74.7,74.4,73.8,73.2,72.2,61.9��

Claims (4)

1. the method synthesizing alpha-aromatic sulfur glycosides, it is characterised in that comprise the following steps: at solvent N, in dinethylformamide, with alpha-glycosyl mercaptan for substrate, with tetrabutyl ammonium bromide for part, under Hydro-Giene (Water Science). catalysis, react to obtain alpha-aromatic sulfur glycosides with iodo aromatic hydrocarbon; Reaction equation is as follows:
2. the method synthesizing alpha-aromatic sulfur glycosides as claimed in claim 1, it is characterised in that reaction temperature is 80 DEG C.
3. the method synthesizing alpha-aromatic sulfur glycosides as claimed in claim 2, it is characterised in that reaction system has been additionally added potassium phosphate.
4. the method synthesizing as claimed in claim 3 alpha-aromatic sulfur glycosides, it is characterised in that concrete technology comprises the steps: to be placed in two neck round-bottomed flasks by Hydro-Giene (Water Science)., tetrabutyl ammonium bromide, potassium phosphate, iodo aromatic hydrocarbon, evacuation, changes nitrogen three times; Being dissolved in N in nitrogen atmosphere, the alpha-glycosyl thiol solution in N-dimethylformamide solvent adds in round-bottomed flask; Being placed in oil bath by round-bottomed flask, be warming up to 80 DEG C of reaction 4h, reaction is down to room temperature after terminating, and adds saturated aqueous common salt cancellation reaction, adds saturated aqueous common salt and ethyl acetate, extract separatory, merge organic facies, then dry with anhydrous sodium sulfate in round-bottomed flask; Concentrating under reduced pressure, residue passes through column chromatography sharp separation, obtains alpha-aromatic sulfur glycosides.
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Publication number Priority date Publication date Assignee Title
CN108659063A (en) * 2018-05-25 2018-10-16 西北大学 A kind of preparation method of 2- nitros galactolipin sulphur glycoside derivates
CN112279880A (en) * 2019-07-23 2021-01-29 四川大学 Novel glycosyl donor, thioglycoside compound and preparation method thereof
CN114349803A (en) * 2022-01-17 2022-04-15 江西师范大学 Method for synthesizing thioglycoside
CN114349803B (en) * 2022-01-17 2023-05-16 江西师范大学 Method for synthesizing thioglycoside

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