Practical synthesis of 1&; prime; -substituted Tubercidin C-nucleoside analogs

Several 1\'-substituted analogs of Tubercidin C-nucleosides were prepared using a highly convergent synthesis. Good to high diastereoselectivity was achieved using a variety of nucleophiles targeting the 1\'-position. The source for this stereoselectivity is herein proposed. It is thought...

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Bibliographic Details
Published inTetrahedron letters Vol. 53; no. 5; pp. 484 - 486
Main Authors Metobo, Sammy E, Xu, Jie, Saunders, Oliver L, Butler, Thomas, Aktoudianakis, Evangelos, Cho, Aesop, Kim, Choung U
Format Journal Article
LanguageEnglish
Published 01.02.2012
Subjects
Analogs
Chelation
Ethers
Nucleophiles
Ribose
Stereoselectivity
Synthesis (chemistry)
Tetrahedrons
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Summary:Several 1\'-substituted analogs of Tubercidin C-nucleosides were prepared using a highly convergent synthesis. Good to high diastereoselectivity was achieved using a variety of nucleophiles targeting the 1\'-position. The source for this stereoselectivity is herein proposed. It is thought to be attributed to a temperature-dependent chelation of the incoming nucleophile to either the 2\'- or 3\'-benzyloxy ether of the ribose core.
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SourceType-Scholarly Journals-1
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ISSN:0040-4039
DOI:10.1016/j.tetlet.2011.11.055