Record Details

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

EPrints@IICB

View Archive Info
 
 
Field Value
 
Title Nucleoside Synthesis from 3-alkylated sugars: Role of 3b-oxy Substituents in Directing Nucleoside Formation
 
Creator Sahabuddin, Sk
Ghosh, Ramprasad
Achari, Basudeb
Mandal, Sukhendu B
 
Subject Chemistry
 
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.
 
Date 2006
 
Type Article
PeerReviewed
 
Format application/pdf
 
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.
 
Relation http://dx.doi.org/10.1039/b514028e
http://www.eprints.iicb.res.in/442/