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Toward L-Homo-DNA: Stereoselective de Novo Synthesis of beta-L-erythro-Hexopyranosyl Nucleosides

  作者 DALONZO DANIELE; GUARAGNA ANNALISA; VAN AERSCHOT ARTHUR; HERDEWIJN PIET; PALUMBO GIOVANNI  
  选自 期刊  Journal of Organic Chemistry;  卷期  2010年75-19;  页码  6402-6410  
  关联知识点  
 

[摘要]A novel route to 2',3'-dideoxy-beta-L-erythro-hexopyranosyl nucleosides equipped with a 1'-(N-6-benzoyl-adenin-9-yl) or a 1'-(thymin-l-yl) moiety has been developed. Synthesis of the enantiopure sugar moiety was carried out by a de novo approach based on a domino reaction as the key step. N-Glycosidation was explored via either nucleobase-transfer mechanism (B = T) or in situ anomerization (B = A or T), affording target nucleosides with high overall stereoselectivity.

 
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