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Synthesis of LeXand LeYOligosaccharides with Azido-Type Spacer-Arms. Comparison of 3- and 4-Methoxybenzyl Groups as Key Temporary Protective Groups1

 

作者: SantiagoFigueroa Pérez,   RaulGonzález Lio,   VioletaFernández Santana,   VicenteVerez Bencomo,  

 

期刊: Journal of Carbohydrate Chemistry  (Taylor Available online 1998)
卷期: Volume 17, issue 6  

页码: 835-850

 

ISSN:0732-8303

 

年代: 1998

 

DOI:10.1080/07328309808007459

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

5-Azido-3-oxa-l-pentanol was prepared from 2-(2-chloroethoxy)ethanol and used as a spacer in the chemical synthesis of the trisaccharide β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc and the tetrasaccharide α-L-Fuc-α-(1→2)-β-D-Gal-(1→4)-[α-L-Fuc-(1→3)]-GlcNAc that represent the epitopes defining the human blood groups Lexand Ley. The classical 4-methoxybenzyl group and the remarably acid-stable 3-methoxybenzyl group were compared as temporary protective groups for position 3 at the glucosamine unit to circumvent the problems associated with the simultaneous presence of allyl and azido groups. The resulting oligosaccharides were coupled to proteins with high efficiency.

 

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