Stable D-xylose ditriflate in divergent syntheses of dihydroxy prolines, pyrrolidines, tetrahydrofuran-2-carboxylic acids, and cyclic sugar -amino acids

17 June 2022, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Double nucleophilic displacement of a sugar D-xylose ditriflate derived from diacetone-D-glucose by amines, water and alkyl cyanoacetates gave a series of bicyclic divergent intermediates for the synthesis of a wide range of highly functionalized targets, including hydroxylated prolines, pyrrolidines, THF carboxylic acids, and cyclopentanes

Keywords

sugars
prolines
iminosugars
furans
beta-amino acids
cyanoacetic acid synthesis
asymmetric synthesis
b-peptides

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