d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening

R. D. Guthrie, Ian D. Jenkins, San Thang, James J. Watters, Ryohei Yamasaki

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5 Citations (Scopus)

Abstract

The epoxide ring of methyl 3,4-anhydro-β-d-tagatofuranoside is opened byattack of nucleophiles at C-4 to yield derivatives of D-fructose. Treatment of 2,3-O-isopropylidene-1,6-di-Op-tolylsulfonyl-β-d-fructofuranose with sulfuryl chloride resulted in attack at C-6, not C-4. 2,3-O-Isopropylidene-1,6-di-O-p-tolylsulfonyl-β-d-tagatofuranose behaved normally with this reagent. Methyl 4-deoxy-β-d-threo-hexulofuranoside was not hydrolysed by invertase.

Original languageEnglish
Pages (from-to)1-6
Number of pages6
JournalCarbohydrate Research
Volume103
Issue number1
DOIs
Publication statusPublished - 1 May 1982

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