STEREOSELECTIVE SYNTHESES OF ALKYL-ALPHA-SIALOSIDES AND ALKYL-2-THIO-ALPHA-SIALOSIDES

被引:19
作者
LUBINEAU, A
LEGALLIC, J
机构
[1] Institut de Chimie Moleculaire d'Orsay, Universite Paris-Sud, F-91405 ORSAY CEDEX
关键词
D O I
10.1080/07328309108543905
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Alkyl and thioalkyl alpha-glycosides of N-acetylneuraminic acid have been prepared in near quantitative yield and with complete stereoselectivity, under the Williamson reaction conditions using RONa or RSNa, respectively, in ROH or RSH as solvent.
引用
收藏
页码:263 / 268
页数:6
相关论文
共 12 条
[1]  
AUGE C, 1988, NEW J CHEM, V12, P733
[2]   C-13 NMR-SPECTRAL STUDY OF THE MODE OF BINDING OF MN-2+ AND GD-3+ TO N-ACETYL-ALPHA-NEURAMINIC ACID [J].
DAMAN, ME ;
DILL, K .
CARBOHYDRATE RESEARCH, 1982, 102 (APR) :47-57
[3]   SYNTHESIS OF PARA-NITROPHENYL 5-ACETAMIDO-3,5-DIDEOXY-ALPHA-D-GLYCERO-D-GALACTO-2-NONULOPYRANOSIDONIC ACID, A CHROMOGENIC SUBSTRATE FOR SIALIDASES [J].
ESCHENFELDER, V ;
BROSSMER, R .
CARBOHYDRATE RESEARCH, 1987, 162 (02) :294-297
[4]   STUDIES ON THE THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID .1. SYNTHESIS OF ALKYL ALPHA-GLYCOSIDES OF 2-THIO-N-ACETYLNEURAMINIC ACID [J].
HASEGAWA, A ;
NAKAMURA, J ;
KISO, M .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1986, 5 (01) :11-19
[5]   STUDIES ON THE THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID .5. GLYCOSYLATION USING METHYLTHIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID AND DIMETHYL(METHYLTHIO)SULFONIUM TRIFLATE [J].
KANIE, O ;
KISO, M ;
HASEGAWA, A .
JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (02) :501-506
[6]   SYNTHESE ANOMERER SIALINSAURE-METHYLKETOSIDE [J].
KUHN, R ;
LUTZ, P ;
MACDONALD, DL .
CHEMISCHE BERICHTE-RECUEIL, 1966, 99 (02) :611-+
[7]   STEREOSELECTIVE SYNTHESIS OF 2-THIOGLYCOSIDES OF N-ACETYLNEURAMINIC ACID [J].
MARRA, A ;
SINAY, P .
CARBOHYDRATE RESEARCH, 1989, 187 (01) :35-42
[8]   UBER SYNTHETISCHE KETOSIDE DER N-ACETYL-D-NEURAMINSAURE .1. DARSTELLUNG EINER REIHE DURCH NEURAMINIDASE SPALTBARER KETOSIDE [J].
MEINDL, P ;
TUPPY, H .
MONATSHEFTE FUR CHEMIE UND VERWANDTE TEILE ANDERER WISSENSCHAFTEN, 1965, 96 (03) :802-&
[9]   SYNTHESES OF 2-O-GLYCOSYL DERIVATIVES OF N-ACETYL-D-NEURAMINIC ACID .3. - STUDIES ON SIALIC ACIDS [J].
OGURA, H ;
FURUHATA, K ;
ITOH, M ;
SHITORI, Y .
CARBOHYDRATE RESEARCH, 1986, 158 :37-51
[10]   PHASE-TRANSFER-CATALYZED SYNTHESIS OF ARYL ALPHA-KETOSIDES OF N-ACETYLNEURAMINIC ACID - A 2-METHYLFLUORAN-6-YL GLYCOSIDE OF N-ACETYLNEURAMINIC ACID, 2-METHYL-6-(5-ACETAMIDO-3,5-DIDEOXY-ALPHA-D-GLYCERO-D-GALACTO-NONULOPYRANOSYLONIC ACID)XANTHENE-9-SPIRO-1'-ISOBENZOFURAN-3'-ONE, A NEW SUBSTRATE FOR NEURAMINIDASE ASSAY [J].
ROTHERMEL, J ;
FAILLARD, H .
CARBOHYDRATE RESEARCH, 1990, 196 :29-40