HALOENAMINES .2. A RAPID AND EFFICIENT SYNTHESIS OF CARBOHYDRATE 1,2-ORTHOESTERS

被引:14
作者
ERNST, B
DEMESMAEKER, A
WAGNER, B
WINKLER, T
机构
[1] Central Research Laboratories, CIBA-GEIGY Ltd.
关键词
D O I
10.1016/S0040-4039(00)97015-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Carbohydrate exo 1,2-orthoesters are obtained in good to excellent yields by treating furanose and pyranose hemiacetals first with 1.1 eq. 1-chloro-2,N,N-trimethyl-propenylamine and then with the appropriate alcohols in the presence of NEt3. © 1990.
引用
收藏
页码:6167 / 6170
页数:4
相关论文
共 24 条
[1]   AN EFFICIENT AND STEREOSELECTIVE SYNTHESIS OF 3,4,6-TRI-O-ACETYL-ALPHA-D-GLUCOPYRANOSE 1,2-[EXO-ALKYL ORTHOACETATES] [J].
BANOUB, J ;
BOULLANGER, P ;
POTIER, M ;
DESCOTES, G .
TETRAHEDRON LETTERS, 1986, 27 (35) :4145-4148
[2]   1,2-ORTHOACETATE INTERMEDIATES IN SILVER TRIFLUOROMETHANESULFONATE PROMOTED KOENIGS-KNORR SYNTHESIS OF DISACCHARIDE GLYCOSIDES [J].
BANOUB, J ;
BUNDLE, DR .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1979, 57 (16) :2091-2097
[3]   SUGAR ORTHO ESTERS .8. SYNTHESIS OF 4-ORTHO-METHYL-D-GLUCURONIC ACID-DERIVATIVES [J].
BOCHKOV, AF ;
VOZNYI, YV .
CARBOHYDRATE RESEARCH, 1974, 32 (01) :1-8
[4]   SILVER IMIDAZOLATE-ASSISTED GLYCOSIDATION .5. SYNTHESIS OF CARBOHYDRATE ORTHO-ESTERS [J].
DAHLIN, BM ;
GAREGG, PJ ;
JOHANSSON, R ;
SAMUELSSON, B ;
ORN, U .
ACTA CHEMICA SCANDINAVICA SERIES B-ORGANIC CHEMISTRY AND BIOCHEMISTRY, 1981, 35 (09) :669-670
[5]   SYNTHESIS OF ACYL HALIDES UNDER VERY MILD CONDITIONS [J].
DEVOS, A ;
REMION, J ;
FRISQUEHESBAIN, AM ;
COLENS, A ;
GHOSEZ, L .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (24) :1180-1181
[6]   PREPARATION OF GLYCOSYL HALIDES UNDER NEUTRAL CONDITIONS [J].
ERNST, B ;
WINKLER, T .
TETRAHEDRON LETTERS, 1989, 30 (23) :3081-3084
[7]  
Fischer E., 1920, BER, V53, P2362
[8]  
GORIN PAJ, 1982, CARBOHYD RES, V101, P12
[9]  
HANESSIAN S, 1975, CARBOHYD RES, V44, pC14
[10]   SYNTHESEN VON GLYKOSIDEN IM HOMOGENEN MEDIUM [J].
HELFERICH, B ;
DOPPSTADT, A ;
GOTTSCHLICH, A .
NATURWISSENSCHAFTEN, 1953, 40 (16) :441-442