Synthesis and reactivity of benzyl 2-0-trifluoromethyl-sulfonyl-and benzyl 3-o-trifluoromethylsulfonyl-β-d-ribofuranoside - the first evidence of tri fluoromethyl - sulfonyl (triflyl) migration in carbohydrates

Barbara Nawrot, Krzysztof W. Pankiewicz, Robert A. Zepf, Kyoichi A. Watanabe

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Abstract

Benzyl 2,5-di-O-(tert-butyldimethyl)silyl-3-O-triflyl-β-D-ribofuranoside (13) underwent triflyl migration upon O-desilylation with triethylammonium hydrogen fluoride in tetrahydrofuran affording benzyl 2-O-triflyl-β-D-ribo-furanoside (7) in ca. 5% yield, together with three other products, benzyl 3-O-triflyl-β-D-ribofuranoside (17), benzyl 2-O-(tert-butyldimethyl)silyl-3-O- triflyl-β-D-ribo-furanoside (18) and benzyl 3-deoxy-β-D- glvceropento-furanos-2-uloside (16). In order to confirm the triflyl migration, a series of reactions were performed.

Original languageEnglish (US)
Pages (from-to)95-114
Number of pages20
JournalJournal of Carbohydrate Chemistry
Volume7
Issue number1
DOIs
StatePublished - Mar 1988

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Funding Information:
was supported in part by funds from the National Cancer Institnte,

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