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Action of Base on Methyl 6-Thio- (and 6-Deoxy-) 2-O-Methanesulfonyl-α-d-Glucopyranoside Derivatives1

 

作者: Isidoro Izquierdo,   Miguel Rodríguez,   MaríaT. Plaza,   Julia Pleguezuelos,  

 

期刊: Journal of Carbohydrate Chemistry  （Taylor Available online 1998）
卷期: Volume 17, issue 1  

页码: 61-74

 

ISSN:0732-8303

 

年代: 1998

 

DOI:10.1080/07328309808005769

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

Treatment of methyl 4-O-benzoyl-3-O-tert-butyldiphenylsilyl-2-O-methanesulfonyl-6-thio-α-d-glucopyranoside (8) and its 6-deoxy analogue (11) with methanolic sodium methoxide, afforded methyl 2,3-anhydro-mannopyranoside derivatives as a consequence of an O3→ O4TBDPS rearrangement. When the protecting group at C-3 was 2-methoxyethoxy methyl ether only deacylation and methanolysis of the methanesulfonyl group occurred.

 

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