Synthetic studies on a potential endoglycosidase inhibitor: Chemical conversion of N,N'-diacetylchitobiose into a pseudodisaccharide containing 2-acetamido-1,2-dideoxynojirimycin

被引：7
|
作者：
Takahashi, S [1 ]
Terayama, H [1 ]
Kuzuhara, H [1 ]
机构：
[1] SAITAMA UNIV,FAC ENGN,DEPT FUNCT MAT SCI,URAWA,SAITAMA 338,JAPAN
来源：
TETRAHEDRON | 1996年 / 52卷 / 42期
关键词：
GLUCOSIDASE INHIBITOR; CHITINASE INHIBITOR; YEAST CHITINASE; DISACCHARIDES; DERIVATIVES; 2-ACETAMIDO-1,5-IMINO-1,2,5-TRIDEOXY-D-MANNITOL; DEMETHYLALLOSAMIDIN; 1-DEOXYNOJIRIMYCIN; ALLOSAMIDIN; ANALOGS;
D O I：
10.1016/0040-4020(96)00791-0
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The usefulness of N,N'-diacetylchitobiose (1) as a starting material for syntheses of biologically active compounds was shown by converting allyl chitobioside 5 into O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-(1-->4)-2-acetamido-1,2,5-trideoxy-1,5-imino-D-glucitol (2), which would be a potential glycosidase inhibitor. The conversion includes a discriminative modification of two amino groups existing in the disaccharide intermediate 8, regioselective introduction of an azide group and construction of a piperidine ring utilizing an intramolecular aminocyclization. Copyright (C) 1996 Elsevier Science Ltd
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页码：13315 / 13326
页数：12
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