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A Direct Organocatalytic Entry to Selectively Protected Aldopentoses and Derivatives

✍ Scribed by Christoph Grondal; Dieter Enders

Publisher: John Wiley and Sons
Year: 2007
Tongue: English
Weight: 184 KB
Volume: 349
Category: Article
ISSN: 1615-4150
DOI: 10.1002/adsc.200600573

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✦ Synopsis

Abstract

The proline‐catalysed aldol reaction of 2,2‐dimethyl‐1,3‐dioxan‐5‐one with dimethoxyacetaldehyde is used as the key reaction according to the biomimetic C~3~+C~n~ strategy for de novo carbohydrate synthesis. Based on the Whitesides inversion strategy, protected D‐erythro‐pentos‐4‐ulose (de>96 %, ee=94 %) was employed for a rapid and divergent entry to various selectively and partly orthogonal protected aldopentoses and derivatives, like amino sugars, thio sugars, deoxy sugars, 4‐C‐substituted (alkylated) aldopentoses and epoxy sugars.

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