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US 5,627,272 AGranted
Process for preparing sugar acetonides
AssigneeBoehringer Ingelheim GmbH
InventorsRainer Sobotta, Franz Dietrich Klinger, Heinrich Schneider
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Abstract
A method of preparing sugar acetonides, such as for example 1,2:5,6-Di-O-isopropylidene-.alpha.-D-glucofuranose, by reacting the corresponding sugar, e.g. D-(+)-glucose, with acetone in the presence of a Lewis acid and a carboxylic acid derivative of general formula ##STR1## wherein X is a leaving group which may be readily replaced by a hydroxyl group.
Claims15
A process for preparing an acetonide of a monosaccharide comprising the steps of
- (a) reacting a monosaccharide with acetone in the presence of a Lewis acid and a carboxylic acid derivative of the formula ##STR5## wherein X is a leaving group and R.sup.1 is methyl, ethyl, propyl, isopropyl, butyl, pentyl, or hexyl to produce a reaction mixture;
- (b) cooling the reaction mixture;
- (c) contacting the cooled reaction mixture produced in step (b) with a dilute aqueous solution of an alkali or alkaline earth metal to form a solution;
- (d) extracting the solution produced in step (c) with an aliphatic or aromatic hydrocarbon to produce a combined extract;
- and
- (e) isolating the acetonide of a monosaccharide from the combined extract of step (d).
3 more elements
A process for preparing 1,2-5,6-diacetone-D-glucose from a monosaccharide comprising the steps of:
- (a) reacting D-glucose with acetone in the presence of a Lewis acid and a carboxylic acid derivative of the following formula ##STR6## wherein X is a leaving group and R.sup.1 is methyl, ethyl, propyl, isopropyl, butyl, pentyl or hexyl at a temperature in the range of 40.degree. to 58.degree. C.;
- (b) cooling the reaction mixture of step (a);
- (c) contacting the cooled reaction mixture with a dilute aqueous solution of an alkali or alkaline earth metal;
- (d) extracting the resulting mixture with an aliphatic or aromatic hydrocarbon;
- (e) combining the extracts of step (d);
- (f) heating the combined extracts of step (e) to a temperature in the range of 50.degree. to 60.degree. C.;
- (g) combining the heated combined extracts of step (f) with a precipitating agent;
- and
- (h) precipitating the product 1,2-5,6-diacetone-D-glucose.
6 more elements
Dependencies are inferred from the claim text.