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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