A NEW EFFICIENT ACYLATION OF FREE GLYCOSYLAMINES

被引:12
作者
LEONRUAUD, P [1 ]
ALLAINMAT, M [1 ]
PLUSQUELLEC, D [1 ]
机构
[1] ECOLE NORMALE SUPER CHIM RENNES,CHIM ORGAN & SUBSTANCES NAT,CNRS,AVE GEN LECLERC,F-35700 RENNES,FRANCE
关键词
D O I
10.1016/S0040-4039(00)74271-7
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Acylations of free glycosylamines 1-3 using 3-acyl(or alkoxycarbonyl)-5-methyl-1,3,4-thiadiazole-2(3H)-thiones 5 and 2-acylthio-5-methyl-1,3,4-thiadiazoles 6 as acylating reagents, provided high yields of N-acyl-glycosylamines, whereas reactions with 3-acyl-thiazolidine-2-thiones 4 caused drastic deglycosylations.
引用
收藏
页码:1557 / 1560
页数:4
相关论文
共 23 条
[11]   UBER N-GLYKOSIDE [J].
HELFERICH, B ;
MITROWSKY, A .
CHEMISCHE BERICHTE-RECUEIL, 1952, 85 (01) :1-8
[12]   NOVEL IMIDAZOLE DERIVATIVE FROM 2-ACETAMIDO-2-DEOXY-N-P-TOLYL-BETA-D-GLUCOPYRANOSYLAMINE [J].
HIRANO, S ;
YAMASAKI, R .
CARBOHYDRATE RESEARCH, 1975, 43 (02) :377-379
[13]   STRUCTURAL INFLUENCE OF SUGAR AND AGLYCON MOIETIES ON ACETOLYSIS OF SOME GLYCOSYLAMINES [J].
HIRANO, S ;
YAMASAKI, R .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1975, 39 (05) :995-998
[14]   MUTAROTATION, HYDROLYSIS, AND REARRANGEMENT REACTIONS OF GLYCOSYLAMINES [J].
ISBELL, HS ;
FRUSH, HL .
JOURNAL OF ORGANIC CHEMISTRY, 1958, 23 (09) :1309-1319
[15]   SYNTHESIS OF GLYCOSYLAMIDES AND 4-N-GLYCOSYL-L-ASPARAGINE DERIVATIVES [J].
KHORLIN, AY ;
ZURABYAN, SE ;
MACHARADZE, RG .
CARBOHYDRATE RESEARCH, 1980, 85 (02) :201-208
[16]   SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS [J].
KUNZ, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04) :294-308
[17]   *NEUE DARSTELLUNGSMETHODEN FUR 1-AMINO-ZUCKER UND EINIGE IHRER N-SUBSTITUTIONSPRODUKTE [J].
MICHEEL, F ;
FRIER, R ;
PLATE, E ;
HILLER, A .
CHEMISCHE BERICHTE-RECUEIL, 1952, 85 (11) :1092-1096
[18]  
NAGAO Y, 1984, CHEM PHARM BULL, V32, P2687
[19]  
NAGAO Y, 1980, TETRAHEDRON LETT, P841
[20]   SUGAR CHEMISTRY WITHOUT PROTECTIVE GROUPINGS .1. REGIOSELECTIVE ESTERIFICATION OF ANOMERIC HYDROXYL OF LACTOSE, MALTOSE AND GLUCOSE [J].
PLUSQUELLEC, D ;
ROULLEAU, F ;
BERTHO, F ;
LEFEUVRE, M ;
BROWN, E .
TETRAHEDRON, 1986, 42 (09) :2457-2467