An Unusual Behavior of Methyl or Benzyl 3-Azido-5-O-Benzoyl-3,6-Di-Deoxy-α-L-Talofuranoside with (Dimethylamino)Sulfur Trifluoride; Migration of the Alkoxyl Group from the C-1 to the C-2 Position
作者:
Akira Hasegawa,
Makoto Goto,
Makoto Kiso,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1985)
卷期:
Volume 4,
issue 4
页码: 627-638
ISSN:0732-8303
年代: 1985
DOI:10.1080/07328308508082680
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
The reaction of methyl or benzyl 3-azido-5-0-benzoyl-3,6-di-deoxy-α-L-talofuranoside with (diethylamino)sulfur trifluoride (DAST) in toluene at 60°C resulted in the formation of 3-azido-5-0-benzoyl-3,6-dideoxy-2-0-methyl (or 2-0-benzyl)-3β-L-galactofuranosyl fluoride in good yield. In this reaction the alkoxyl group at C-1 migrated to the C-2 position and a fluorine atom entered into the C-1 position. The furanosyl fluoride was converted,viareduction of the azido group followed byN-trifluoroacetylation, acetolysis, andO-deacetylation, into 3,6-dideoxy-2-0-methyl-3-trifluoroacet-amido-L-galactopyranose (2-methoxy-Daunosamine derivative).
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