Tetrahedron

Diastereospecific synthesis of 2′-or 3′-c-branched nucleosides through intramolecular free-radical capture by silicon-tethered acetylene

Z Xi, J Rong, J Chattopadhyaya

文献索引：Xi, Zhen; Rong, Jianhui; Chattopadhyaya, Jyoti Tetrahedron, 1994 , vol. 50, # 17 p. 5255 - 5272

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被引用次数: 30

摘要

The intramolecular free-radical trapping by a silicon tethered acetylene function in a ribonucleoside 2a, 2b, 2c, 8a, 8b or 8c gave only the [3.3. 0]-cis-fused Z-vinylsiloxane 3a, 3b, 3c, 9a, 9b or 9c (&> 90%) in a diastereospecific manner. The temporary silicon connection from the Z-vinylsiloxane was removed by the oxidation to give the 2′-or 3′-C-branched α- keto-, β-D-ribonucleoside (∼ 85%), which was diastereospecifically reduced to give 1, 3- ...