Journal ArticleDOI
A Novel Aspect in Chlorination of D-Glucal Derivatives. Important Roles of the 4,6-O-Benzylidene Group and Substituent at C-3 in the Selective Formation of β-D-Manno and β-D-Arabino Isomers
Reads0
Chats0
TLDR
In contrast with the precedent reports described in peracetyl and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4-6-Obenzylonidene-Dglucalin in carbon tetrachloride predominantly occurred from the β-side to give the β -D-manno and β-Darabino adducts, respectively.Abstract:
In contrast with the precedent reports described in peracetyl-and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4,6-O-benzylidene-D-glucal in carbon tetrachloride predominantly occurred from the β-side to give the β-D-manno and β-D-arabino adducts, respectively.read more
Citations
More filters
Journal ArticleDOI
Electrochemical bromochlorination of peracetylated glycals.
TL;DR: 2-bromo-2-deoxy-glycopyranosyl chlorides were obtained in high yields and were generated electrochemically from a mixture of bromides and chlorides in dichloromethane.
Journal ArticleDOI
A Novel Aspect in Chlorination of D-Glucal Derivatives. Important Roles of the 4,6-O-Benzylidene Group and Substituent at C-3 in the Selective Formation of β-D-Manno and β-D-Arabino Isomers.
TL;DR: In contrast with the precedent reports described in peracetyl and perbenzyl-D-glucal, chlorination of 3-O-acetyl- and 3-deoxy-4-6-Obenzylonidene-Dglucalin in carbon tetrachloride predominantly occurred from the β-side to give the β -D-manno and β-Darabino adducts, respectively.
References
More filters
Journal ArticleDOI
The mechanisms of the halogenations and halogenomethoxylations of d-glucal triacetate, d-galactal triacetate, and 3,4-dihydropyran
R. U. Lemieux,B. Fraser-Reid +1 more
TL;DR: The stereochemical routes of the reactions showed trends, when the halogen, the olefin, and the solvent were changed, which can be accounted for on the basis of the relative stabilities of the... as mentioned in this paper.
Journal ArticleDOI
Addition reactions of glycals. V. Solvent effects in the chlorine addition to D-glucal triacetate
Journal ArticleDOI
Additions comparées des halogenès sur le 3,4,6-tri-O-acétyl-1,5-anhydro-1,5-didésoxy-, d-arabino-hex-1-énitol et l'analogue 3,4,6-tri-O-benzylé; effets de solvant sur la formation spécifique des dérivés 1,2-didésoxy-1,2-dihalogéno-α-d-glucopyranoses
Paul Boullanger,Gérard Descotes +1 more
TL;DR: In this article, a comparison of the addition of chlorine and bromine to 3,4,6-tri-O -acetyl-1,5-anhydro-1-5-dideoxy- d - arabino -hex-l-enitol analogs was made.
Related Papers (5)
THE PREPARATION OF 4,6-O-BENZYLIDENE-D-GLUCAL AND THE REACTION OF METHYLLITHIUM WITH METHYL 2,3-ANHYDRO-4,6-O-BENZYLIDENE-α-D-ALLOPYRANOSIDE
M. Sharma,R. K. Brown +1 more