1,2-trans Glycosylation via Neighboring Group Participation of 2- O-Alkoxymethyl Groups: Application to One-Pot Oligosaccharide Synthesis

Milandip Karak, Yohei Joh, Masahiko Suenaga, Tohru Oishi, Kohei Torikai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The use of 2-O-alkoxymethyl groups as effective stereodirecting substituents for the construction of 1,2-trans glycosidic linkages is reported. The observed stereoselectivity arises from the intramolecular formation of a five-membered cyclic architecture between the 2-O-alkoxymethyl substituent and the oxocarbenium ion, which provides the expected facial selectivity. Furthermore, the observed stereocontrol and the extremely high reactivity of 2-O-alkoxymethyl-protected donors allowed development of a one-pot sequential glycosylation strategy that should become a powerful tool for the assembly of oligosaccharides.

Original languageEnglish
Pages (from-to)1221-1225
Number of pages5
JournalOrganic letters
Volume21
Issue number4
DOIs
Publication statusPublished - Feb 15 2019

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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