Nucleoside Synthesis from 3-alkylated sugars: Role of 3b-oxy Substituents in Directing Nucleoside Formation

Sahabuddin, Sk and Ghosh, Ramprasad and Achari, Basudeb and Mandal, Sukhendu B (2006) Nucleoside Synthesis from 3-alkylated sugars: Role of 3b-oxy Substituents in Directing Nucleoside Formation. Organic & Biomolecular Chemistry, 4 (3). pp. 551-557.

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    Abstract

    Using Vorbr¨uggen’s protocol, reaction of persilylated uracil with xylofuranose derivatives having 3b-oxy-3a-alkyl substitution produced both a- and b-nucleosides. Only the b-nucleosides were formed from substrates having the reverse stereochemistry at C-3 or lacking the 3-alkyl substituent. Participation of the 3b-oxy substituent in stabilizing the incipient C-1 carbonium ion (or oxonium ion) intermediate has been suggested from analysis of energy-minimized conformations.

    Item Type: Article
    URI: http://www.eprints.iicb.res.in/id/eprint/442
    Subjects: Chemistry
    Divisions: Indian Institute of Chemical Biology
    Depositing User: Ms Sutapa Ganguly
    Date Deposited: 01 Nov 2011 15:04
    Last Modified: 07 Feb 2012 11:37
    Official URL: http://dx.doi.org/10.1039/b514028e
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