N-Aryl-O-glycosyl Haloacetimidates as Glycosyl Donors

被引:32
作者
Huchel, Uschi [1 ]
Tiwari, Pallavi [1 ]
Schmidt, Richard R. [1 ]
机构
[1] Univ Konstanz, Fachbereich Chem, Dept Chem, D-78457 Constance, Germany
关键词
Carbohydrates; Glycosidation; N-Aryl-O-glycosyl haloacetimidates; Synthesis; O-Imidoylation; ACTIVATION; REAGENT; PROMOTER; TRIFLATE;
D O I
10.1080/07328301003597673
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Reaction of 1-O-unprotected tetra-O-acetyl- and tetra-O-benzyl-glucopyranose with N-aryl haloacetimidoyl chlorides in the presence of sodium hydride and 15-crown-5 afforded N-aryl-O-glucopyranosyl haloacetimidates. Mainly the -anomers were obtained in this anomeric O-acylation-type reaction. The glycosyl donor properties of these haloacetimidates were investigated with 6-O- and 4-O-unprotected glucopyranosides as acceptors. The results were compared with those obtained with the corresponding O-glucopyranosyl trichloroacetimidates as glycosyl donors and the same acceptors. It was found that N-(2-chloro-6-methylphenyl)-O-glucopyranosyl trifluoroacetimidates (16Ad, 16Bd) exhibit glycosyl donor properties closely related to those of the corresponding N-unsubstituted O-glucopyranosyl trichloroacetimidates (12A, 12B).
引用
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页码:61 / 75
页数:15
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