SYNTHESIS OF NEW GLUCOSIDE SURFACTANTS USING HALOGENATED SUGARS - THIOETHER AND SULFONE DERIVATIVES OF METHYL ALPHA-D-GLUCOSIDE AND METHYL ALPHA-D-MANNOSIDE

被引:21
作者
LEONRUAUD, P [1 ]
PLUSQUELLEC, D [1 ]
机构
[1] ECOLE NATL SUPER CHIM RENNES,CNRS,CHIM ORGAN & SUBST NAT LAB,AVE GEN LECLERC,F-35700 RENNES,FRANCE
关键词
D O I
10.1016/S0040-4020(01)87130-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We describe an efficient synthesis of methyl 6-halogeno-6-deoxyglycosides which was performed using Ph3P-X2 in DMF solution. Carbohydrate halides could thus be isolated in high yields without preliminary protection of the secondary hydroxyl groups, and were used as intermediates for the preparation of 6-alkylthio- and 6-alkylsulfonyl-6-deoxy glycosides. These derivatives are new non-ionic chiral surfactants.
引用
收藏
页码:5185 / 5192
页数:8
相关论文
共 30 条
[1]   C-13 NUCLEAR MAGNETIC-RESONANCE SPECTROSCOPY OF MONOSACCHARIDES [J].
BOCK, K ;
PEDERSEN, C .
ADVANCES IN CARBOHYDRATE CHEMISTRY AND BIOCHEMISTRY, 1983, 41 :27-66
[2]  
BOECKMAN RK, 1974, TETRAHEDRON LETT, P913
[3]  
CASTRO B, 1973, B SOC CHIM FR II-CH, P3034
[4]  
CASTRO B, 1972, TETRAHEDRON LETT, P5001
[5]   ALKYLOXYPHOSPHONIUM SALTS .7. SELECTIVE ACTIVATION OF ALPHA,ALPHA-TREHALOSE AND SACCHAROSE [J].
CASTRO, B ;
CHAPLEUR, Y ;
GROSS, B .
CARBOHYDRATE RESEARCH, 1974, 36 (02) :412-419
[6]  
CASTRO BR, 1983, ORG REACTIONS, V29, P1
[7]   CONVERSION OF HYDROXYL-GROUPS INTO BROMO GROUPS IN CARBOHYDRATES WITH INVERSION OF CONFIGURATION [J].
CLASSON, B ;
GAREGG, PJ ;
SAMUELSSON, B .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02) :339-343
[8]   NEW HALOGENATION REAGENT SYSTEMS USEFUL FOR THE MILD ONE-STEP CONVERSION OF ALCOHOLS INTO IODIDES OR BROMIDES [J].
CLASSON, B ;
LIU, ZC ;
SAMUELSSON, B .
JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (26) :6126-6130
[9]   VIROSOMES RECONSTITUTED FROM HUMAN-IMMUNODEFICIENCY-VIRUS PROTEINS AND LIPIDS [J].
CORNET, B ;
VANDENBRANDEN, M ;
COGNIAUX, J ;
GIURGEA, L ;
DEKEGEL, D ;
RUYSSCHAERT, JM .
BIOCHEMICAL AND BIOPHYSICAL RESEARCH COMMUNICATIONS, 1990, 167 (01) :222-231
[10]   A PHOSPHORUS NUCLEAR-MAGNETIC-RESONANCE SPECTROSCOPIC STUDY OF THE CONVERSION OF HYDROXY-GROUPS INTO IODO GROUPS IN CARBOHYDRATES USING THE IODINE TRIPHENYLPHOSPHINE IMIDAZOLE REAGENT [J].
GAREGG, PJ ;
REGBERG, T ;
STAWINSKI, J ;
STROMBERG, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (03) :271-274