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An Efficient Method for the Synthesis of β-d-Ribonucleosides Catalyzed by Metal Iodides#

 

作者: Teruaki Mukaiyama,   Masashi Nagai,   Takafumi Matsutani,   Naoyuki Shimomura,  

 

期刊: Nucleosides and Nucleotides  (Taylor Available online 1996)
卷期: Volume 15, issue 1-3  

页码: 17-30

 

ISSN:0732-8311

 

年代: 1996

 

DOI:10.1080/07328319608002367

 

出版商: Taylor & Francis Group

 

数据来源: Taylor

 

摘要:

Several β-d-ribonucleosides were synthesized in high yields under mild conditions byN-glycosylations of methyl 2,3,5-tri-O-benzoyl-β-d-ribofuranosyl carbonate (1) with trimethylsilylated nucleoside bases in acetonitrile using a catalytic amount of metal iodide such as SnI2, SbI3or TeI4. A deprotection ofN6-benzoyl group of coupling product took place to a considerable extent whenN6-benzoyl-N6,N9-bis(trimethylsilyl)adenine was employed as a nucleoside base using SnI2or SnCI2as a catalyst while it was minimized when SbI3or TeI4was used. Further, theN-glycosylation of1with 7-trimethylsilyltheophylline in the presence of a catalytic amount of metal iodide was more effectively achieved in nitrile solvents other than acetonitrile.

 

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