Stereoselective glycosylation of 3-deoxy-d-manno-2-octulosonic acid with batch and microfluidic methods

Atsushi Shimoyama, Yukari Fujimoto, Koichi Fukase

Research output: Contribution to journalArticlepeer-review

16 Citations (Scopus)

Abstract

A practical and efficient stereoselective synthesis of 3-deoxy-d-manno-2- octulosonic acid (Kdo) glycoside was achieved using N-trifluoroacetoimidate as the glycosyl donor with both batch and microfluidic methods. The method used a conformationally constrained glycosyl donor, which has a bulky isopropylidene group at the 4,5-O-position. The strained conformation directed the coordination of the acetonitrile solvent, which led to the enhancement of reactivity and -selectivity in the glycosylation.

Original languageEnglish
Article numberU04811ST
Pages (from-to)2359-2362
Number of pages4
JournalSynlett
Issue number16
DOIs
Publication statusPublished - 2011 Sep 15
Externally publishedYes

Keywords

  • carbocation
  • carbohydrates
  • glycosylation
  • natural products
  • stereoselective synthesis

ASJC Scopus subject areas

  • Organic Chemistry

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