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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
Working Paper
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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Version History

Jun 17, 2022 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv-2022-qstvl
D O I: 10.26434/chemrxiv-2022-qstvl [opens in a new tab]

Funding

European Regional Development Fund
ERDF

Author’s competing interest statement

The author(s) have declared they have no conflict of interest with regard to this content

Ethics

The author(s) have declared ethics committee/IRB approval is not relevant to this content

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