The reaction of methyl 4, 6-O-isopropylidene-2, 3-O-thiocarbonyl-α-D-mannoside with methyl iodide: a synthesis of methyl α-Tyveloside (methyl 3, 6-dideoxy-α-D- …

JJ Patroni, BW Skelton, RV Stick, RV White

Index: Patroni, Joseph J.; Skelton, Brian W.; Stick, Robert V.; White, Allan H. Australian Journal of Chemistry, 1980 , vol. 33, # 5 p. 987 - 999

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Citation Number: 8

Abstract

Abstract The reaction of methyl 4, 6-O-isopropylidene-2, 3-O-thiocarbonyl-α-D-mannoside with methyl iodide gives two major products, methyl 3, 6-dideoxy-3, 6-diiodo-2-O- (methylthio) carbonyl-α-D-altro-pyranoside and methyl 2, 3-O-carbonyl-6-deoxy-6-iodo-α-D- mannopyranoside, both of which lack the 4, 6-O-isopropylidene grouping but contain the 6- deoxy-6-iodo function, and another minor product. One of the major products, methyl 3, 6- ...