Application of PPh3/CI3CCONH2 towards the Glycosylation of Glycosyl Hamiacetals
Application of PPh3/CI3CCONH2 towards the Glycosylation of Glycosyl Hamiacetals
摘要
Triphenylphosphine coupled with trichloroacetamide was determined to be an effective reagent for the conversion of 2,3,4,6-tetra-O-benzyl-D-glucopyranose as a glycosyl hemiacetal to the corresponding glycosyl chloride in excellent yield under mild and neutral conditions. Subsequently, the glycosyl chloride was reacted with alcohol or glycosyl acceptors in the presence of zinc（ll） bromide and molecular sieve 5 A to afford the corresponding glycosides in high yields and a-selectivity. This practical and convenient protocol can be utilized for the one-pot glycosylation of glycosyl hemiacetals.
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