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

doi:10.1080/07328308808058906

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

Center for Drug Design

Research output: Contribution to journal › Article › peer-review

15 Scopus citations

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 language	English (US)
Pages (from-to)	95-114
Number of pages	20
Journal	Journal of Carbohydrate Chemistry
Volume	7
Issue number	1
DOIs	https://doi.org/10.1080/07328308808058906
State	Published - Mar 1988

Bibliographical note

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

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10.1080/07328308808058906

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Nawrot, B., Pankiewicz, K. W., Zepf, R. A., & Watanabe, K. A. (1988). 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. Journal of Carbohydrate Chemistry, 7(1), 95-114. https://doi.org/10.1080/07328308808058906

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. / Nawrot, Barbara; Pankiewicz, Krzysztof W.; Zepf, Robert A. et al.
In: Journal of Carbohydrate Chemistry, Vol. 7, No. 1, 03.1988, p. 95-114.

Research output: Contribution to journal › Article › peer-review

Nawrot, B, Pankiewicz, KW, Zepf, RA & Watanabe, KA 1988, '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', Journal of Carbohydrate Chemistry, vol. 7, no. 1, pp. 95-114. https://doi.org/10.1080/07328308808058906

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title = "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",

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.",

author = "Barbara Nawrot and Pankiewicz, \{Krzysztof W.\} and Zepf, \{Robert A.\} and Watanabe, \{Kyoichi A.\}",

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AU - Pankiewicz, Krzysztof W.

AU - Zepf, Robert A.

AU - Watanabe, Kyoichi A.

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N2 - 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.

AB - 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.

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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

Abstract

Bibliographical note

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