The first chemical synthesis of 6-thio-d-fructo-pyranose via methyl 6-bromo-6-deoxy-1,3-o-isopro-pylidene-α-d-fructofuranoside as a key intermediate

Tadashi Hanaya, Nobuaki Sato, Hiroshi Yamamoto

Research output: Contribution to journalArticle

Abstract

Selective bromination of sucrose, followed by acetalation with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, afforded methyl 6-bromo-6-deoxy-1,3-O-isopropylidene-α-d-fructofuranoside (4). The first chemical synthesis of 6-thio-d-fructopyranose was accomplished from 4 through its 6-S-acetyl-6-thio derivative.

Original languageEnglish
Pages (from-to)517-522
Number of pages6
JournalHeterocycles
Volume71
Issue number3
DOIs
Publication statusPublished - Mar 1 2007

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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