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

Research output: Contribution to journalArticleResearchpeer-review

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

Cite this

Guthrie, R. D. ; Jenkins, Ian D. ; Thang, San ; Watters, James J. ; Yamasaki, Ryohei. / d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening. In: Carbohydrate Research. 1982 ; Vol. 103, No. 1. pp. 1-6.
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d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening. / Guthrie, R. D.; Jenkins, Ian D.; Thang, San; Watters, James J.; Yamasaki, Ryohei.

In: Carbohydrate Research, Vol. 103, No. 1, 01.05.1982, p. 1-6.

Research output: Contribution to journalArticleResearchpeer-review

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T1 - d-fructose derivatives modified at C-4 by direct displacementand by oxirane opening

AU - Guthrie, R. D.

AU - Jenkins, Ian D.

AU - Thang, San

AU - Watters, James J.

AU - Yamasaki, Ryohei

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AB - 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.

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