A general method for the synthesis of sugar 2-C-sulfonic acids by 1 → 2 arylthio group migration in acid-sensitive thioglycosides. Direct transformation of thiotrityl ethers into C-sulfonic acids

András Lipták, Ferenc Sajtos, Lóránt Jánossy, Diethmar Gehle, László Szilágyi

Research output: Contribution to journalArticle

20 Citations (Scopus)

Abstract

(Matrix presented) Fully protected triphenylmethyl 2-O-mesyl-1-thio-β- D-gluco- (14) and -α-D-mannopyranoside (28) were transformed by a stereoselective intramolecular 1 → 2 trans-arylthio migration into methyl 2-S-triphenylmethyl-α-D-manno- (15) and -β-D-glucopyranoside (29), respectively, using NaOCH3 as nucleophile. The 2-S-triphenylmethyl ethers (15 and 29) were directly oxidized to sugar 2-C-sulfonic acids by using oxone (2KHSO5, KHSO4, K2SO4). Compounds (21, 23, 32, and 35) are the first representatives of secondary sugar C-sulfonic acids.

Original languageEnglish
Pages (from-to)3671-3674
Number of pages4
JournalOrganic Letters
Volume5
Issue number20
DOIs
Publication statusPublished - Oct 2 2003

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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