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A method for preparing 1,2-oxygen-isopropylidene-alpha-d-6,3-glucuronolactone

A technology of -alpha-d-6 and isopropylidene, applied in the field of sugar chemistry, can solve the problems of multiple reaction steps, complex process, high risk, etc., and achieve the effect of high selectivity, simple process and convenient operation

Active Publication Date: 2020-05-08
SYNGARS TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the existing technology currently has the following disadvantages: many reaction steps, each step needs to be purified or crystallized, the process is complicated, many solvents are used, the risk is high, the yield is low, and the cost is high

Method used

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  • A method for preparing 1,2-oxygen-isopropylidene-alpha-d-6,3-glucuronolactone
  • A method for preparing 1,2-oxygen-isopropylidene-alpha-d-6,3-glucuronolactone

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Effect test

Embodiment 1

[0030] The invention provides a method for preparing 1,2-oxo-isopropylidene-alpha-D-6,3-glucuronolactone, comprising the following steps:

[0031] (1) Propylene protection reaction: Add 10 grams of glucose and 40 grams of hydrogen-type cation exchange resin to 500 milliliters of acetone, heat at 55°C and stir for 6 hours, cool to 25°C, add 200 milliliters of water, and continue the reaction at room temperature After 5 hours, filter off the resin, and recover acetone under vacuum at 50°C to obtain 1,2-oxo-isopropylidene-alpha-D-glucose solution;

[0032] (2), uronic acid oxidation reaction: 0.1 g of 10% platinum carbon is added to 1,2-oxo-isopropylidene-alpha-D-glucose solution, and 10% sodium hydroxide solution is added dropwise at 55°C for control The pH value is 9, the pressure is maintained at 0.01MPa by feeding oxygen, and the catalyst is recovered by filtration for 6 hours. The filtrate is vacuum concentrated at 50°C to a concentration of 35%, and the sodium ion is remove...

Embodiment 2

[0035] The invention provides a method for preparing 1,2-oxo-isopropylidene-alpha-D-6,3-glucuronolactone, comprising the following steps:

[0036] (1) Propylene protection reaction: Add 10 grams of glucose and 15 grams of hydrogen-type cation exchange resin to 250 milliliters of acetone, heat at 30°C and stir for 12 hours, cool to 25°C, add 50 milliliters of water, and continue the reaction at room temperature After 2 hours, the resin was filtered off, and acetone was recovered under vacuum at 50°C to obtain 1,2-oxo-isopropylidene-alpha-D-glucose solution;

[0037] (2), uronic acid oxidation reaction: 0.3 grams of 5% platinum carbon is added to 1,2-oxo-isopropylidene-alpha-D-glucose solution, and 10% sodium hydroxide solution is added dropwise at 35°C for control PH value 10, feed oxygen to maintain pressure 0.01MPa, stir vigorously for 3 hours, filter and recover the catalyst, concentrate the filtrate in vacuum at 50°C to 20% concentration, pass through cation exchange resin ...

Embodiment 3

[0040] The invention provides a method for preparing 1,2-oxo-isopropylidene-alpha-D-6,3-glucuronolactone, comprising the following steps:

[0041] (1) Propylene protection reaction: Add 10 grams of glucose and 30 grams of hydrogen-type cation exchange resin to 400 milliliters of acetone, heat at 40°C and stir for 9 hours, cool to 25°C, add 100 milliliters of water, and continue the reaction at room temperature After 3 hours, the resin was filtered off, and acetone was recovered under vacuum at 50°C to obtain 1,2-oxo-isopropylidene-alpha-D-glucose solution;

[0042](2), uronic acid oxidation reaction: 0.2 g of 5% platinum carbon is added to 1,2-oxo-isopropylidene-alpha-D-glucose solution, and 10% sodium hydroxide solution is added dropwise at 30°C for control PH value 11, feed oxygen to maintain pressure 0.01MPa, stir vigorously for 2 hours, filter and recover the catalyst, concentrate the filtrate in vacuum at 50°C to 30% concentration, pass through cation exchange resin to re...

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Abstract

The invention discloses a method for preparing 1,2-O-isopropylidene-alpha-D-glucofuranuronic acid-3-lactone. The method comprises the following steps: successively completing glucose mono-propyliden protection; catalytically oxidizing platinum carbon into mono-propyliden glucuronic acid; extracting, concentrating and lactonizing by using an organic solvent A; gradually cooling and crystallizing in an organic solvent B, thus obtaining the 1,2-O-isopropylidene-alpha-D-glucofuranuronic acid-3-lactone. The 1,2-O-isopropylidene-alpha-D-glucofuranuronic acid-3-lactone disclosed by the invention is prepared by adopting a one-pot method, the technological steps are simple, an intermediate is not required to be purified, the operation is convenient, solvents are few, and the yield is high.

Description

technical field [0001] The invention belongs to the field of sugar chemistry, and in particular relates to a method for preparing 1,2-oxo-isopropylidene-alpha-D-6,3-glucuronolactone. Background technique [0002] 1,2-Oxo-isopropylidene-alpha-D-6,3-glucuronolactone, also known as D-glucuronic acid-γ-lactone acetone compound, the English name is 1,2-O-isopropylidene -a-D-Glucofuranuronic Acid-3-Lactone, CAS number: 20513-98-8, molecular formula: C10H14O5. [0003] Regarding the method for preparing 1,2-oxo-isopropylidene-alpha-D-6,3-glucuronolactone, the existing technical method is divided into five steps, and the first step is to react glucose and methanol for methyl Protection to obtain glucuronic acid, the second step is to oxidize glucuronic acid to uronic acid to obtain methyl glucuronic acid, the third step is to demethylate methyl glucuronic acid to obtain glucuronic acid, and the fourth step Glucuronide is used to obtain glucuronolactone, and the fifth step is to re...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H9/04C07H1/00
CPCC07H1/00C07H9/04Y02P20/584
Inventor 陈红辉
Owner SYNGARS TECH CO LTD
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