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beta-Selective Arabinofuranosylation Using a 2,3-O-Xylylene-Protected Donor

  作者 IMAMURA AKIHIRO; LOWARY TODD L  
  选自 期刊  Organic Letters;  卷期  2010年12-16;  页码  3686-3689  
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[摘要]Reported is a novel stereoselective beta-arabinofuranosylation that makes use of a conformationally restricted 2,3-O-zylylene-protected arabinofuranosyl donor. Optimization of the reaction conditions showed that factors including the structure of the acceptor alcohol, substrate concentration, and protecting group on O-5 of the donor affect the stereochemical outcome of the glycosylation. To demonstrate the utility of the methodology, the synthesis of an oligosaccharide fragment from the mycobacterial cell wall polysaccharide lipoarabinomannan was carried out.

 
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