First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates

Gefei Li, Masato Noguchi, Kensuke Nakamura, Ryohei Hayasaka, Yuuki Tanaka, Shin ichiro Shoda

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)

Abstract

A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.

Original languageEnglish
Pages (from-to)3428-3431
Number of pages4
JournalTetrahedron Letters
Volume59
Issue number37
DOIs
Publication statusPublished - 2018 Sep 12

Keywords

  • 1-Deoxy sugar
  • Direct anomeric activation
  • Glycosyl dithiocarbamate
  • Protection-free synthesis
  • Radical desulfurization

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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