Nucleoside Synthesis from 3-alkylated sugars: Role of 3b-oxy Substituents in Directing Nucleoside Formation
IR@IICB: CSIR-Indian Institute of Chemical Biology, Kolkata
View Archive Info| Field | Value | |
| Title |
Nucleoside Synthesis from 3-alkylated sugars: Role of 3b-oxy Substituents in Directing Nucleoside Formation
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| Creator |
Sahabuddin, Sk
Ghosh, Ramprasad Achari, Basudeb Mandal, Sukhendu B |
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| Subject |
Chemistry
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| Description |
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.
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| Date |
2006
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| Type |
Article
PeerReviewed |
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| Format |
application/pdf
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| Identifier |
http://www.eprints.iicb.res.in/442/1/ORGANIC_%26_BIOMOLECULAR_CHEMISTRY%2C_4(_3)%2C_551%2D5%2C[130].pdf
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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| Relation |
http://dx.doi.org/10.1039/b514028e
http://www.eprints.iicb.res.in/442/ |
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