An easy access to anomeric glycosyl amides and imines (Schiff bases) via transformation of glycopyranosyl trimethylphosphinimides

被引:56
作者
Kovács, L
Osz, E
Domokos, V
Holzer, W
Györgydeák, Z
机构
[1] Univ Debrecen, Dept Organ Chem, H-4010 Debrecen, Hungary
[2] Univ Pecs, Dept Med Chem, H-7624 Pecs, Hungary
[3] Univ Vienna, Inst Pharmazeut Chem, Pharm Zentrum, A-1090 Vienna, Austria
关键词
glycosyl amides; glycosyl imines; glycosyl imides; Staudinger reaction;
D O I
10.1016/S0040-4020(01)00380-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation and application of anomeric glycosyl phosphinimides in preparative synthesis were studied. Starting from the appropriate glycosyl azides and trialkyl or triaryl phosphines, the corresponding phosphinimides were obtained by modified Staudinger reactions. The latter compounds were readily converted into 1-N-acyl-gluco- and galactopyranosyl amines with high yields by applying activated acid derivatives or simple carboxylic acids. 1-N-Alkylidene- or arylidenephosphinimines (Schiff bases) were obtained by means of aza-Wittig reactions using aliphatic or aromatic aldehydes, respectively. (C) 2001 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:4609 / 4621
页数:13
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