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

TY - JOUR

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

EP - 1283

JO - Journal of the Chemical Society, Perkin Transactions 1

JF - Journal of the Chemical Society, Perkin Transactions 1

IS - 7

ER -