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Issue 3, 2006
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Nucleoside synthesis from 3-alkylated sugars: role of 3β-oxy substituents in directing nucleoside formation

Sk. Sahabuddin,a  Ramprasad Ghosh,a  Basudeb Acharia  and  Sukhendu B. Mandal*a 
Author affiliations

* Corresponding authors

a Department of Medicinal Chemistry, Indian Institute of Chemical Biology, Kolkata, India
E-mail: sbmandal@iicb.res.in

Abstract

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

Graphical abstract: Nucleoside synthesis from 3-alkylated sugars: role of 3β-oxy substituents in directing nucleoside formation

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Publication details

The article was received on 03 Oct 2005, accepted on 30 Nov 2005 and first published on 05 Jan 2006


Article type: Paper
DOI: 10.1039/B514028E
Citation: Org. Biomol. Chem., 2006,4, 551-557
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    Nucleoside synthesis from 3-alkylated sugars: role of 3β-oxy substituents in directing nucleoside formation

    Sk. Sahabuddin, R. Ghosh, B. Achari and S. B. Mandal, Org. Biomol. Chem., 2006, 4, 551
    DOI: 10.1039/B514028E

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