Synthesis of Azide-armed α-1-C-Alkyl-imino-d-xylitol Derivatives as Key Building Blocks for the Preparation of Iminosugar Click Conjugates

…, D Rodríguez-Lucena, P Compain

Index: Decroocq, Camille; Laparra, Laura Mamani; Rodriguez-Lucena, David; Compain, Philippe Journal of Carbohydrate Chemistry, 2011 , vol. 30, # 7-9 p. 559 - 574

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Citation Number: 13

Abstract

Azide-armed α-1-C-alkyl-imino-d-xylitol derivatives have been efficiently prepared by way of olefin cross-metathesis in eight to nine steps and in an overall yield of 19% to 26% from 2, 3, 4-tri-O-benzyl-d-xylopyranose. Optimization of cleavage conditions of N-NAP-protected tertiary amines using DDQ in CH2Cl2-H2O (18: 1) is also reported. The iminosugars synthesized will be used as key building blocks in the synthesis of multivalent iminosugars ...