期刊
CARBOHYDRATE RESEARCH
卷 341, 期 16, 页码 2641-2652出版社
ELSEVIER SCI LTD
DOI: 10.1016/j.carres.2006.08.023
关键词
glycals; chlorodifluoromethylation; fluorinated sugars; C-Cl-bond activation; radical hydrodechlorination; radical allylation
The dithionite-mediated addition of BrCF2Cl to 3,4-di-O-pivaloyl-D-xylal (1) generated preferably 1-CF2Cl-substituted products, that is, (2-bromo-2-deoxy-3,4-di-O-pivaloyl-beta-D-xylopyranosyl)-chlorodifluoromethane and (2-deoxy-3,4-di-O-pivaloyl-beta-D-threo-pentopyranosyl)-chlorodifluoromethane. Selected chlorodifluorornethyl-substituted monosaccharide derivatives were hydrodechlorinated or alkylated at the CF2Cl-group using tin reagents under radical reaction conditions. Thus, hydrodechlorinations of (2,3,4-tri-O-acetyl-6-deoxy-alpha-L-gal actopyranosyl)-chlorodifluoromethane and of methyl 3,4-di-O-acetyl-2-C-chlorodifluoromethyl-2,6-dideoxy-alpha/beta-L-glucopyranoside are reported using tri-n-butyltin hydride initiated by AIBN. UV-initiated allylations are reported for reactions of (2-deoxy-3,4-di-O-pivaloyl-beta-D-threo-pentopyranosyl)-chlorodifluoromethane, (2,3,4-tri-O-acetyl-6-deoxy-alpha-L-galactopyranosyl)-chlorodifluoromethane, 1,3,4,6-tetra-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha-D-glucopyranose, 1,3,4,6-tetra-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha-D-mannopyranose and methyl 3,4-di-O-acetyl-2-C-chlorodifluoromethyl-2-deoxy-alpha/beta-D-rabinopyranoside with allyltri-n-butyltin. (c) 2006 Elsevier Ltd. All rights reserved.
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