Ring opening method of pyranose ring as well as product and application thereof
A technology of pyranose ring and glucopyranoside, applied in the field of ring-opening of pyranose ring, can solve the problems of unfriendly environment, harsh reaction conditions, etc., and achieve the effects of environmental friendliness, mild reaction conditions, and enhanced internal tension
- Summary
- Abstract
- Description
- Claims
- Application Information
AI Technical Summary
Problems solved by technology
Method used
Image
Examples
Embodiment 1
[0069] A kind of ring-opening method of glucopyranoside, the synthetic route is:
[0070]
[0071] Include the following steps:
[0072] S1. Dichloromethane (30 mL) was added stoichiometrically to a round bottom flask (100 mL) and 5 equiv of pyridine (1.7 mL, 0.021 mmol) was added. Subsequently, a dichloromethane solution (10 mL) containing sulfonyl chloride (0.87 mL, 0.011 mmol) was added dropwise, methyl-α-D-glucopyranoside (1 g, 0.005 mmol) was added, and the solution was heated at room temperature (15-25 °C). After 24 hours of reaction, the reaction was judged to be complete by thin layer chromatography (petroleum ether: ethyl acetate=7:3), the solution was filtered and distilled under reduced pressure to obtain the crude product; the crude product was subjected to silica gel column chromatography (petroleum ether: ethyl acetate) =9:1) purification, fractions were concentrated to give compound II as a white amorphous solid (yield 0.72 g, 47.7%).
[0073] 1 H NMR (600...
Embodiment 2
[0079] A kind of ring-opening method of glucopyranoside, the synthetic route is:
[0080]
[0081] Include the following steps:
[0082] S1. Weigh methyl-α-D-glucopyranoside (5g, 0.026mmol) according to the stoichiometric ratio and add it to the round bottom flask (500mL), then add N,N-dimethylformamide (150mL), After fully dissolving, 2,2-dimethoxypropane (15.83 mL, 0.129 mmol) was added at room temperature, and p-toluenesulfonic acid was used as a catalyst (0.01 g) to react at 40 °C for 18 h, through thin layer chromatography Judging that the reaction was complete (petroleum ether:ethyl acetate=0:1), after the system was cooled, the N,N-dimethylformamide was spin-dried in vacuo, ethyl acetate was added to the system to dilute, and the combined organic layers were washed with brine , dried over anhydrous sodium sulfate, and distilled under reduced pressure to obtain the crude product; the crude product was purified by silica gel column chromatography (petroleum ether:ethy...
Embodiment 3
[0095]
[0096] Include the following steps:
[0097] S1. Weigh compound III (1 g, 0.0023 mmol) according to the stoichiometric ratio and add it to the round-bottomed flask (50 mL), then add 10 mL of tetrahydrofuran, after fully dissolving, add 2 mL of concentrated hydrochloric acid with a mass fraction of 38% at room temperature, 35° C. The reaction was carried out for 15h, and it was judged that the reaction was complete by thin-layer chromatography (methanol:ethyl acetate=1:1). After the system was cooled, the pH was adjusted to 5-7 with sodium bicarbonate, distilled under reduced pressure and spin-dried, and added to the system. Absolute ethanol, filtered and concentrated under reduced pressure to obtain Intermediate VI;
[0098] S2. Add 5 mL of N,N-dimethylformamide to compound VI (0.6 g, 0.0022 mol), after fully dissolving, add 4 times benzaldehyde dimethyl acetal (1.31 ml, 0.0088 mmol), and add 2 drops of methane dropwise Sulfonic acid, react at room temperature (15...
PUM
Login to View More Abstract
Description
Claims
Application Information
Login to View More - R&D
- Intellectual Property
- Life Sciences
- Materials
- Tech Scout
- Unparalleled Data Quality
- Higher Quality Content
- 60% Fewer Hallucinations
Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.
© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com