Nucleoside synthesis from 3-alkylated sugars: role of 3 beta-oxy substituents in directing nucleoside formation
Metadata of CSIR Papers
View Archive Info| Field | Value | |
| Title |
Nucleoside synthesis from 3-alkylated sugars: role of 3 beta-oxy substituents in directing nucleoside formation
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| Creator |
Sahabuddin, S
Ghosh, R Achari, B Mandal, SB |
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| Subject |
Chemistry, Organic
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| Description |
Using Vorbruggen's protocol, reaction of persilylated uracil with xylofuranose derivatives having 3 beta-oxy-3 alpha-alkyl substitution produced both alpha- and beta-nucleosides. Only the beta-nucleosides were formed from substrates having the reverse stereochemistry at C-3 or lacking the 3-alkyl substituent. Participation of the 3 beta-oxy substituent in stabilizing the incipient C-1 carbonium ion (or oxonium ion) intermediate has been suggested from analysis of energy-minimized conformations.
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| Publisher |
ROYAL SOC CHEMISTRYCAMBRIDGETHOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
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| Date |
2011-09-20T12:12:20Z
2011-09-20T12:12:20Z 2006 |
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| Type |
Article
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| Identifier |
ORGANIC & BIOMOLECULAR CHEMISTRY
1477-0520 http://hdl.handle.net/123456789/14232 |
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| Language |
English
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