Reaction of 1,2-0-Alkylidenehexofuranurono-6,3-Lactones with Diethylaminosulfur Trifluoride (DAST)
作者:
R. Albert,
K. Dax,
U. Katzenbeisser,
H. Sterk,
A.E. Stütz,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 4
页码: 521-528
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508082674
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Reaction of 1,2-0-alkylidenehexofuranurono-6,3-lactones with diethylaminosulfur trifluoride (DAST) led to 1,2-0-alkylidene-5-deoxy-5-fluorohexofuranurono-6,3-lactones (13–30%) together with 1,2-0-alkylidene-3,6-anhydro-6,6-difluorohexofuranoses (45–58%). Evidence was found for participation of the hydroxyl group at C-5 in the formation of the difluorides. Trifluoro compounds could not be prepared by reaction with DAST but were formed from the difluorides by triflate formation and displacement using tetra-n-butylammonium fluoride.
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