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Process for Scale-up Preparation of α-Acetobromoglucos1 and Its Reaction with Aliphatic Alcohols

Milana Lawzer, Y. L. (2010) Process for Scale-up Preparation of α-Acetobromoglucos1 and Its Reaction with Aliphatic Alcohols. [Student Project Report]

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Abstract

This Dissertation / Report is the outcome of investigation carried out by the creator(s) / author(s) at the department/division of Central Food Technological Research Institute (CFTRI), Mysore mentioned below in this page.

Item Type: Student Project Report
Additional Information: From the above discussion it is evident that, synthesis of naturally occurring glycosides by chemical methods is a very important process. The Koenigs-Knorr method is general and applicable to synthesis of various glycosides. In this method the glycosyl donar is usually in the form halides such as 2,3,4,6-tetra-O-acetyl-α-D-glucopranosyl bromide, 2,3,4,6-tetra-O-acetyl-α-D-glucopranosyl chloride, and various galacto- & fructo- 5 pyranosyl halides. These halides are activated by various reagents such as AgOTf, Ag2CO3, AgClO4, Ag2CO3, Hg(CN)2, HgBr2, and Hg(CN)2 to attach with aglycon part. Synthesis of glycosyl halides as a starting materials for Koenigs-Knorr synthesis of glycosides also an important process. Of the various glycosides synthesized, the 2,3,4,6-tetra-O-acetyl-α-D-glucopranosyl bromide has been found to be used in extensively. The literature method of synthesis of the 2,3,4,6-tetra-O-acetyl-α-D-glucopranosyl bromide involves α-D-glucose, phosphorus and bromine. The procedure followed are cumbersome and leads to low yield of the product. The product prepared this way needs to be utilized as quickly as possible or otherwise it decomposes to mixture of compounds. This limitation has been addressed and synthesized title compound by Heena on a small scale.
Uncontrolled Keywords: glycosides; aromatic alcohols; Koenigs-Knorr method; Glycosidation Methods
Subjects: 500 Natural Sciences and Mathematics > 04 Chemistry and Allied Sciences > 31 Sugar Chemistry
Divisions: Plantation Products Spices and Flavour Technology
Depositing User: Food Sci. & Technol. Information Services
Date Deposited: 07 Sep 2010 11:30
Last Modified: 28 Dec 2011 10:17
URI: http://ir.cftri.com/id/eprint/9637

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