Organic letters

Synthesis of α-glucuronic acid and amide derivatives in the presence of a participating 2-acyl protecting group

M Tosin, PV Murphy

Index: Tosin, Manuela; Murphy, Paul V. Organic Letters, 2002 , vol. 4, # 21 p. 3675 - 3678

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Citation Number: 68

Abstract

Participating acyl groups located at C-2 in glucosyl and related donors generally promote formation of 1, 2-trans-glycosides. Reactions of some glucuronic acid donors with TMSN3/SnCl4 or ROH/SnCl4 gave only the 1, 2-cis-glycoside. The stereoselectivity is consistent with participation of the C-6 group. The methodology was used for the synthesis of a Kdn2en mimetic with the α-configuration.

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