Journal
CARBOHYDRATE RESEARCH
Volume 346, Issue 17, Pages 2683-2687Publisher
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2011.09.016
Keywords
Peracetylated glycals; Bromochlorination; Electrochemical halogenation; Cyclic voltammetry; 2-Bromoglycopyranosyl chlorides
Funding
- Ministry of Education and Science of the Republic of Serbia [172034]
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Peracetylated glycals-3,4,5-tri-O-acetyl-D-glucal (1a), 3,4,5-tri-O-acetyl-D-galactal (1b) and 3,4-di-O-acetyl-6-deoxy-L-glucal (1c)-have been bromochlorinated by a suitable halogenating agent, generated electrochemically from a mixture of bromides and chlorides in dichloromethane. The reaction was performed in two ways: (i) by a constant current electrolysis (2 F mol(-1)) of bromides and substrates in a milieu containing an excess of chlorides (Br(sic)/1/Cl(sic) = 1:1:6.8) and (ii) by anodic generation of free chlorine from chlorides (2 F mol(-1)) and subsequent addition of bromides and substrates in a ratio Br(sic)/1 = 1:1. The corresponding 2-bromo-2-deoxy-glycopyranosyl chlorides were obtained in high yields. (C) 2011 Elsevier Ltd. All rights reserved.
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