D-GALACTOSE-DERIVED D-GALACTURONIC ACID-DERIVATIVES SUITABLE AS GLYCOSYL ACCEPTORS

被引:18
作者
STEFFAN, W [1 ]
VOGEL, C [1 ]
KRISTEN, H [1 ]
机构
[1] UNIV ROSTOCK,SEKT CHEM,BUCHBINDERSTR 9,O-2500 ROSTOCK,GERMANY
关键词
D O I
10.1016/0008-6215(90)84026-Q
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
Allyl (1a) and benzyl (1b) β-d-galactopyranosides were converted into methyl [allyl (and benzyl) 2-O-acetyl-3,4-O-isopropylidene-β-d-galactopyranosid]uronates, (6a and 6b) by three different routes. The carboxyl group was introduced by Jones oxidation of suitably protected precursors and esterified directly. The chemical behaviour of 6-O-trityl-, 6-O-(4,4′-dimethoxytrityl)-, and 6-O-(2-methoxypropane-2-yl)-derivatives was investigated. The overall yields obtained were strongly influenced by the protecting groups used, in particular their stability in acidic solution. © 1990.
引用
收藏
页码:109 / 120
页数:12
相关论文
共 23 条
[1]   SYNTHESIS OF 2,3-4,6-DI-O-ISOPROPYLIDENE DERIVATIVES OF ALKYL-ALPHA-GALACTOPYRANOSIDES AND ALKYL-BETA-D-GALACTOPYRANOSIDES, AND ELUCIDATION OF STRUCTURE BY NMR AND X-RAY-ANALYSIS [J].
BARILI, PL ;
CATELANI, G ;
COLONNA, F ;
MARRA, A ;
CERRINI, S ;
LAMBA, D .
CARBOHYDRATE RESEARCH, 1988, 177 :29-41
[2]   NEW RESULTS IN THE ISOPROPYLIDENATION OF GALACTOPYRANOSIDES - USEFUL INTERMEDIATES FOR THE SYNTHESIS OF GALACTOSE DERIVATIVES [J].
BARILI, PL ;
BERTI, G ;
CATELANI, G ;
COLONNA, F ;
MARRA, A .
TETRAHEDRON LETTERS, 1986, 27 (20) :2307-2310
[3]   SYNTHESIS OF 1,2-O-CYANOETHYLIDENE DERIVATIVES OF ALKYL GLYCOPYRANURONATES BY OXIDATION OF THE 6-TRITYL ETHERS OF THEIR HEXOSE ANALOGS [J].
BETANELI, VI ;
OTT, AY ;
BRUKHANOVA, OV ;
KOCHETKOV, NK .
CARBOHYDRATE RESEARCH, 1988, 179 :37-50
[4]   ASSIGNMENT OF RING SIZE IN ISOPROPYLIDENE ACETALS BY C-13 NMR-SPECTROSCOPY [J].
BUCHANAN, JG ;
EDGAR, AR ;
RAWSON, DI ;
SHAHIDI, P ;
WIGHTMAN, RH .
CARBOHYDRATE RESEARCH, 1982, 100 (MAR) :75-86
[5]   AN IMPROVED PREPARATION OF 3,4-O-ISOPROPYLIDENE DERIVATIVES OF ALPHA-D-GALACTOPYRANOSIDES AND BETA-D-GALACTOPYRANOSIDES [J].
CATELANI, G ;
COLONNA, F ;
MARRA, A .
CARBOHYDRATE RESEARCH, 1988, 182 (02) :297-300
[6]   A NEW TYPE OF CARBOHYDRATE-CONTAINING SYNTHETIC ANTIGEN - SYNTHESIS OF CARBOHYDRATE-CONTAINING POLYACRYLAMIDE COPOLYMERS HAVING THE SPECIFICITY OF O-3 AND O-4 FACTORS OF SALMONELLA [J].
CHERNYAK, AY ;
LEVINSKY, AB ;
DMITRIEV, BA ;
KOCHETKOV, NK .
CARBOHYDRATE RESEARCH, 1984, 128 (02) :269-282
[7]   THE DIRECT CONVERSION OF STEROIDAL DELTA-5-3-BETA-ALCOHOLS TO DELTA-5-KETONES AND DELTA-4-3-KETONES [J].
DJERASSI, C ;
ENGLE, RR ;
BOWERS, A .
JOURNAL OF ORGANIC CHEMISTRY, 1956, 21 (12) :1547-1548
[8]   4-ORTHO-BETA-D-GALACTOPYRANOSYL-3-ORTHO-METHYL-D-GLUCOSE - A NEW SYNTHESIS AND APPLICATION TO THE EVALUATION OF INTESTINAL LACTASE [J].
FERNANDEZMAYORALAS, A ;
MARTINLOMAS, M ;
VILLANUEVA, D .
CARBOHYDRATE RESEARCH, 1985, 140 (01) :81-91
[9]   SYNTHESIS OF HEPARIN FRAGMENTS - A CHEMICAL SYNTHESIS OF THE TRISACCHARIDE O-(2-DEOXY-2-SULFAMIDO-3,6-DI-O-SULFO-ALPHA-D-GLUCOPYRANOSYL)-(1-]4)-O-(2-O-SULFO-ALPHA-L-IDOPYRANOSYLURONIC ACID)-(1-]4)-2-DEOXY-2-SULFAMIDO-6-O-SULFO-D-GLUCOPYRANOSE HEPTASODIUM SALT [J].
JACQUINET, JC ;
PETITOU, M ;
DUCHAUSSOY, P ;
LEDERMAN, I ;
CHOAY, J ;
TORRI, G ;
SINAY, P .
CARBOHYDRATE RESEARCH, 1984, 130 (JUL) :221-241
[10]  
KLOOSTERMAN M, 1985, RECL TRAV CHIM PAY B, V104, P116