C-ALLYLATION OF 1-BROMOSUGAR AND 6-BROMOSUGAR WITH ALLYLIC SULFIDES AND SULFONES

Authors
PONTEN F MAGNUSSON G
Citation
F. Ponten et G. Magnusson, C-ALLYLATION OF 1-BROMOSUGAR AND 6-BROMOSUGAR WITH ALLYLIC SULFIDES AND SULFONES, Journal of organic chemistry, 61(21), 1996, pp. 7463-7466
Citations number
18
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
61
Issue
21
Year of publication
1996
Pages
7463 - 7466
Database
ISI
SICI code
0022-3263(1996)61:21<7463:CO1A6W>2.0.ZU;2-E
Abstract
Reaction of the bromosugars 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyra nosyl bromide (1), methyl 2,3-anhydro-6-bromo-6-deoxy-alpha-D-allopyra noside (2), and methyl 4-O-benzoyl-6-bromo-6-deoxy-alpha-D-allopyranos ide (3) with the-allylic sulfides and sulfones 4-9 in the presence of hexabutyldistannane under photolytic conditions gave the corresponding alpha-C-allyl galactosides 10-12 and the 6-C-allylated epoxysugars 13 , 15, and 16 in 61-90% yield.