An efficient synthesis of methyl 1,3-O-isopropylidene-α-D- fructofuranoside and 2,3:5,6-di-O-isopropylidene-D-glucose dimethyl acetal derivatives from sucrose

Tadashi Hanaya, Nobuaki Sato, Hiroshi Yamamoto

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Acetalation of sucrose with 2,2-dimethoxypropane in 1,4-dioxane in the presence of p-toluenesulfonic acid, followed by acetylation, afforded methyl 4,6-di-O-acetyl-1,3-O-isopropylidene-α-d-fructofuranoside and 4-O-acetyl-2,3:5,6-di-O-isopropylidene-d-glucose dimethyl acetal as major products, while tosylation of the intermediate acetals provided methyl 6-O-tosyl-1,3-O-isopropylidene-α-d-fructofuranose.

Original languageEnglish
Pages (from-to)2494-2501
Number of pages8
JournalCarbohydrate Research
Volume340
Issue number16
DOIs
Publication statusPublished - Nov 21 2005

Keywords

  • Acetalation of sucrose
  • D-Fructofuranoside
  • D-Glucose dimethyl acetal
  • Isopropylidene acetal

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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