Tin mediated regioselective synthesis of sucrose-6-esters

A technology of sucrose and compounds, applied in the direction of sugar derivatives, sugar derivatives, esterified saccharides, etc., can solve problems such as separation troubles

Inactive Publication Date: 2008-02-27
V B MEDICARE PVT LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

To separate the desired sucrose-6-ester from

Method used

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  • Tin mediated regioselective synthesis of sucrose-6-esters
  • Tin mediated regioselective synthesis of sucrose-6-esters
  • Tin mediated regioselective synthesis of sucrose-6-esters

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] Example 1 Preparation of 3-(two O-sucrose) dibutylstannylidene

[0030] Sucrose (200 g) was dissolved in 600 ml of DMF, 145.6 g of DBTO was added, and heated to 80-85°C. This heating was maintained for 10-13 hours to remove the water formed during adduct formation. The reaction mass was cooled and DMF was completely removed by azeotropic distillation. The resulting thick material was treated with 1:2 volumes of dichloromethane.

[0031] The solid formed was filtered and washed with excess dichloromethane. The tin content in the obtained yellow powder was analyzed.

[0032] The same experiment was performed again in the same manner with 200 g of sucrose and 72.8 g of DBTO, and the tin content in the resulting yellow powder was analyzed.

[0033] Analyze these products.

[0034] Analytical Methods and Analysis

[0035] Tin Content Analysis: By Atomic Absorption Spectroscopy

[0036] Other elemental analysis: by CHN analyzer

[0037] Molecular weight analysis: by ...

Embodiment 2

[0046] Example 2 Synthesis of sucrose-6-acetate

[0047] A) In situ formation of sucrose-6-acetate from 3-(diO-sucrose)dibutylstannylidene during the reaction

[0048] Sucrose (200 g) was dissolved in 600 ml of DMF, 72.8 g of DBTO was added, and heated to 80-85°C. This heating was maintained for 10-13 hours to remove the water formed during adduct formation. The reaction mass was then cooled to room temperature and cooled to 0°C. While stirring, 75 ml of acetic anhydride was added dropwise to the reaction mass. The reaction mass was then gradually warmed to room temperature and the acetylation reaction was monitored by frequent TLC analysis. After about 3-4 hours, acetate formation was complete. Then 50ml of water was added to stop the reaction. DBTO in the acetate formed was extracted twice into 1:2 v / v cyclohexane. The layers were then separated and the reaction mass was dehydrated. When the azeotropic distillation of water was complete, sucrose-6-acetate was analyz...

Embodiment 3

[0052] Example 3 Conversion of sucrose to sucrose-6-benzoate using dioctyltin oxide

[0053] Sucrose (20g) was dissolved in 100ml of DMF, 10.6g of dioctyltin oxide was added, and heated to 85-90°C. This heating was maintained for 10-15 hours to remove the water formed during adduct formation. The reaction mass was then cooled to room temperature and cooled to 15°C. 19.8 g (90% purity) of benzoic anhydride was dissolved in 20 ml of DMF and added dropwise to the reaction mass with stirring. The reaction mass was then gradually warmed to room temperature and the benzoylation reaction was monitored by frequent TLC analysis. After about 10-15 hours, benzoate formation was complete. 5 ml of water were then added to terminate the reaction. Dioctyltin oxide in the benzoate formed was extracted twice into 1:2 v / v cyclohexane. The layers were then separated and the reaction mass was dehydrated. When the azeotropic distillation of water was complete, sucrose-6-benzoate was analyz...

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Abstract

A method is disclosed for regioselective synthesis of sucrose-6-acetate via formation of a novel sucrose-tin adduct using sucrose and DBTO. The novel tin adduct can be represented by a formula (6-O-sucrose) - O - Snbutyl.sub.2 -O- (6-O-sucrose) or as 1,3.( di O-sucrose) dibutyl stannylene. The adduct is acylated to yield sucrose-6-acetate or sucrose-6-benzoate as major product.

Description

technical field [0001] The present invention relates to a method and novel strategy for the synthesis of sucrose-6-esters, which are chlorinated sucrose, 1'-6'-dichloro-1'-6'-dideoxy- Precursor of β-fructofuranose-4-chloro-4-deoxy-galactopyranoside (TGS). The present invention also includes a novel method for the synthesis of sucrose-6-esters by a regioselective reaction involving the formation of novel stannylene intermediate compounds. Background technique [0002] The preparation of chlorinated sucrose is a complex process due to the need to perform chlorination at less selective reactive sites on the sucrose molecule in competition with highly selective reactive sites. Generally, this object is achieved by a process which essentially consists of protecting the pyranose ring of the sugar molecule by using various protecting reagents such as anhydrides of alkyl / aryl groups, chlorides of acids, orthoesters, etc. The 6-hydroxyl group in , then chlorinated the protected suc...

Claims

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Application Information

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IPC IPC(8): A23L1/09C07H1/00C07H13/00
CPCC07H13/00C07H1/00C08B31/00C08B31/02
Inventor 拉克什·拉南莫哈莫德·莫菲朱丁森迪普·奥萝拉
Owner V B MEDICARE PVT LTD
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