Reaction of carbohydrates with Vilsmeier reagent: a tandem selective chloro O-formylation of sugars

Niranjan Thota; Debaraj Mukherjee; Mallepally Venkat Reddy; Syed Khalid Yousuf; Surrinder Koul; Subhash Chandra Taneja

doi:10.1039/b900026g

Reaction of carbohydrates with Vilsmeier reagent: a tandem selective chloro O-formylation of sugars

Niranjan Thota, Debaraj Mukherjee, Mallepally Venkat Reddy, Syed Khalid Yousuf, Surrinder Koul, Subhash Chandra Taneja

LUKKET: Institut for Lægemiddeldesign og Farmakologi

14 Citationer (Scopus)

Abstract

A convenient and efficient method for selective replacement of the primary hydroxyl groups of sugars by chlorine with concomitant O-formylation, compatible with the presence of a variety of functional groups, has been developed using the Vilsmeier-Haack reaction. Sugars having free primary hydroxyl groups mostly afforded the chloro-O-formylated product while sugars devoid of primary hydroxyl groups yielded only O-formylated products.

Originalsprog	Engelsk
Tidsskrift	Organic & Biomolecular Chemistry
Vol/bind	7
Udgave nummer	7
Sider (fra-til)	1280-3
Antal sider	4
ISSN	1477-0520
DOI	https://doi.org/10.1039/b900026g
Status	Udgivet - 7 apr. 2009

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10.1039/b900026g

Citationsformater

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title = "Reaction of carbohydrates with Vilsmeier reagent: a tandem selective chloro O-formylation of sugars",

abstract = "A convenient and efficient method for selective replacement of the primary hydroxyl groups of sugars by chlorine with concomitant O-formylation, compatible with the presence of a variety of functional groups, has been developed using the Vilsmeier-Haack reaction. Sugars having free primary hydroxyl groups mostly afforded the chloro-O-formylated product while sugars devoid of primary hydroxyl groups yielded only O-formylated products.",

keywords = "Carbohydrate Conformation, Carbohydrates, Formates, Indicators and Reagents, Stereoisomerism, Journal Article, Research Support, Non-U.S. Gov't",

author = "Niranjan Thota and Debaraj Mukherjee and Reddy, {Mallepally Venkat} and Yousuf, {Syed Khalid} and Surrinder Koul and Taneja, {Subhash Chandra}",

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T1 - Reaction of carbohydrates with Vilsmeier reagent

T2 - a tandem selective chloro O-formylation of sugars

AU - Thota, Niranjan

AU - Mukherjee, Debaraj

AU - Reddy, Mallepally Venkat

AU - Yousuf, Syed Khalid

AU - Koul, Surrinder

AU - Taneja, Subhash Chandra

PY - 2009/4/7

Y1 - 2009/4/7

N2 - A convenient and efficient method for selective replacement of the primary hydroxyl groups of sugars by chlorine with concomitant O-formylation, compatible with the presence of a variety of functional groups, has been developed using the Vilsmeier-Haack reaction. Sugars having free primary hydroxyl groups mostly afforded the chloro-O-formylated product while sugars devoid of primary hydroxyl groups yielded only O-formylated products.

AB - A convenient and efficient method for selective replacement of the primary hydroxyl groups of sugars by chlorine with concomitant O-formylation, compatible with the presence of a variety of functional groups, has been developed using the Vilsmeier-Haack reaction. Sugars having free primary hydroxyl groups mostly afforded the chloro-O-formylated product while sugars devoid of primary hydroxyl groups yielded only O-formylated products.

KW - Carbohydrate Conformation

KW - Carbohydrates

KW - Formates

KW - Indicators and Reagents

KW - Stereoisomerism

KW - Journal Article

KW - Research Support, Non-U.S. Gov't

U2 - 10.1039/b900026g

DO - 10.1039/b900026g

M3 - Journal article

C2 - 19300809

SN - 1470-4358

VL - 7

SP - 1280

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JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 7

ER -

Reaction of carbohydrates with Vilsmeier reagent: a tandem selective chloro O-formylation of sugars

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