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 Article

  

Authors:	Nawrot, B.; Pankiewicz, K. W.; Zepf, R. A.; Watanabe, K. A.
Article 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. © 1988, Taylor & Francis Group, LLC. All rights reserved.
Journal Title:	Journal of Carbohydrate Chemistry
Volume:	7
Issue:	1
ISSN:	0732-8303
Publisher:	Taylor & Francis Group
Date Published:	1988-01-01
Start Page:	95
End Page:	114
Language:	English
DOI:	10.1080/07328308808058906
PROVIDER:	scopus
DOI/URL:	https://www.scopus.com/inward/record.uri?eid=2-s2.0-0642311799&doi=10.1080%2f07328308808058906&partnerID=40&md5=c1b06af5fe56cde5089bbe302ba5c2f0
Notes:	Article -- Source: Scopus

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