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 journalArticlepeer-review

    8 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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