Preparation of Primary and Secondary Azidosugars from Diols using the Dioxaphosphorane Methodology
作者:
Dominique Lafont,
Paul Boullanger,
期刊:
Journal of Carbohydrate Chemistry
(Taylor Available online 1999)
卷期:
Volume 18,
issue 6
页码: 675-688
ISSN:0732-8303
年代: 1999
DOI:10.1080/07328309908544029
出版商: Taylor & Francis Group
数据来源: Taylor
摘要:
Treatment of methyl 2,3-di-O-benzyl-α-D-glucopyranoside (1), methyl 2,3-di-O-acetyl-α-D-glucopyranoside (4), 3-O-benzyl-1,2-O-(1-methylethylidene)-α-D-glucofuranose (6), 3-O-acetyl-1,2-O-(1-methylethylidene)-α-D-glucofuranose (9), 1,2-O-(1-methylethylidene)-α-D-xylofuranose (11) and methyl 2,3-di-O-acetyl-α-D-galactopyranoside (15) with diisopropylazodicarboxylate-triphenylphosphine in tetrahydrofuran led to the corresponding dioxaphosphoranes, which were opened by trimethylsilyl azide affording the silylated primary azidodeoxysugars. When the same reaction was performed on methyl 2,3-di-O-benzyl-α-D-galactopyranoside (20), an inversion of the regioselectivity of the dioxaphosphorane opening was observed, leading mainly to the 4-azido-4-deoxy-α-D-glucopyranoside derivative27.
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