Two efficient routes for construction of amidine-linked pseudo-disaccharide

被引:12
作者
Suzuki, K
Fujii, T
Sato, K
Hashimoto, H
机构
[1] TOKYO INST TECHNOL,DEPT LIFE SCI,FAC BIOSCI & BIOTECHNOL,MIDORI KU,YOKOHAMA,KANAGAWA 226,JAPAN
[2] KANAGAWA UNIV,FAC ENGN,ORGAN CHEM LAB,KANAGAWA KU,YOKOHAMA,KANAGAWA 221,JAPAN
关键词
D O I
10.1016/0040-4039(96)01277-4
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Two routes for the synthesis of the amidine-linked pseudo-disaccharide were developed. The amidine linkage was constructed by the intermolecular or intramolecular coupling between thioamide and amine in the presence of mercury (II) chloride. The former construction from D-arabinono-1,5-thiolactam and 6-amino-6-deoxy-D-glucoside gave the corresponding pseudo-disaccharide. The latter construction of the amidine linkage was demonstrated in the case of 4-(5-amino-5-deoxy-D-thioarabinononyl)amino-4-deoxy-D-glucoside. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:5921 / 5924
页数:4
相关论文
共 15 条
[1]   SYNTHESIS OF GLYCOAMIDINES USING A MERCURY-PROMOTED REACTION [J].
AVALOS, M ;
BABIANO, R ;
CINTAS, P ;
DURAN, CJ ;
JIMENEZ, JL ;
PALACIOS, JC .
TETRAHEDRON, 1995, 51 (29) :8043-8056
[2]  
BESAN J, 1980, SYNTHESIS-STUTTGART, P883
[3]  
BLERIOT Y, 1995, TETRAHEDRON LETT, V36, P5175
[4]   SYNTHESIS OF A BENZYLAMIDINE DERIVED FROM D-MANNOSE - A POTENT MANNOSIDASE INHIBITOR [J].
BLERIOT, Y ;
GENREGRANDPIERRE, A ;
TELLIER, C .
TETRAHEDRON LETTERS, 1994, 35 (12) :1867-1870
[5]   FORMAMID-REAKTIONEN .14. REAKTIONEN VON SAUREAMID-ACYLHALOGENID-ADDUKTEN - DARSTELLUNG SUBSTITUIERTER AMIDINE UND AMIDRAZONE [J].
BREDERECK, H ;
GOMPPER, R ;
KLEMM, K ;
REMPFER, H .
CHEMISCHE BERICHTE-RECUEIL, 1959, 92 (04) :837-849
[6]  
GAUTIER JA, 1975, CHEM AMIDINES IMIDAT, P283
[7]   AMIDINE PSEUDODISACCHARIDES [J].
KNAPP, S ;
CHOE, YH ;
REILLY, E .
TETRAHEDRON LETTERS, 1993, 34 (28) :4443-4446
[8]   A NEW METHOD FOR SYNTHESIS OF PEPTIDES - ACTIVATION OF CARBOXY GROUP WITH DICYCLOHEXYLCARBODIIMIDE AND 3-HYDROXY-4-OXO-3,4-DIHYDRO-1,2,3-BENZOTRIAZINE [J].
KONIG, W ;
GEIGER, R .
CHEMISCHE BERICHTE-RECUEIL, 1970, 103 (07) :2034-&
[9]   AMIDINE, AMIDRAZONE, AND AMIDOXIME DERIVATIVES OF MONOSACCHARIDE ALDONOLACTAMS - SYNTHESIS AND EVALUATION AS GLYCOSIDASE INHIBITORS [J].
PAPANDREOU, G ;
TONG, MK ;
GANEM, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (25) :11682-11690
[10]  
SATCHELL DPN, 1977, CHEM SOC REV, V3, P345