General Homologation Strategy for Synthesis of l -glycero- and d -glycero-Heptopyranoses

Shaheen K. Mulani, Kuang Chun Cheng, Kwok-Kong Mong*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

Abstract

A general and stereospecific homologation strategy for the synthesis of heptopyranosides is reported. The strategy employs the Wittig olefination and proline-catalyzed α-aminoxylation to achieve one carbon elongation and stereoselective hydroxylation at the C6 position, respectively. The l-glycero- and d-glycero-heptopyranosides can be obtained with nearly perfect stereoselectivity. Further study reveals the difference in the chemical shift of the C6 proton of l/d-glycero-heptopyranosyl diastereomers, which is found to be useful for assignment of the configuration of heptopyranosides.

Original languageEnglish
Pages (from-to)5536-5539
Number of pages4
JournalOrganic Letters
Volume17
Issue number22
DOIs
StatePublished - 20 Nov 2015

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