Para-chlorobenzyl protecting groups as stabilizers of the glycosidic linkage: Synthesis of the 3'-O-sulfated Lewis X trisaccharide

被引:32
作者
Pohl, NL [1 ]
Kiessling, LL [1 ]
机构
[1] UNIV WISCONSIN,DEPT CHEM,MADISON,WI 53706
关键词
D O I
10.1016/S0040-4039(97)01670-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The 3'-0-sulfated trisaccharide Lewis x (1) and unsulfated Lewis x (2) have been synthesized using a mute that highlights a more facile regioselective benzylidene ring-opening procedure and the employment of chlorobenzyl groups as a way of strengthening the acid-labile alpha-fucose linkage. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:6985 / 6988
页数:4
相关论文
共 22 条
[1]   Carbohydrate recognition systems: Functional triads in cell-cell interactions [J].
Crocker, PR ;
Feizi, T .
CURRENT OPINION IN STRUCTURAL BIOLOGY, 1996, 6 (05) :679-691
[2]   2 NEW ORTHOGONAL AMINE-PROTECTING GROUPS THAT CAN BE CLEAVED UNDER MILD OR NEUTRAL CONDITIONS [J].
DEBENHAM, JS ;
MADSEN, R ;
ROBERTS, C ;
FRASERREID, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (11) :3302-3303
[3]   Tetrachorophthaloyl as a versatile amine protecting group [J].
Debenham, JS ;
FraserReid, B .
JOURNAL OF ORGANIC CHEMISTRY, 1996, 61 (02) :432-433
[4]   A METHOD FOR THE SELECTIVE REDUCTION OF CARBOHYDRATE 4,6-O-BENZYLIDENE ACETALS [J].
DENINNO, MP ;
ETIENNE, JB ;
DUPLANTIER, KC .
TETRAHEDRON LETTERS, 1995, 36 (05) :669-672
[5]  
GAREGG PJ, 1982, CARBOHYD RES, V108, P97
[6]   A NOVEL, REDUCTIVE RING-OPENING OF CARBOHYDRATE BENZYLIDENE ACETALS, WITH UNUSUAL REGIOSELECTIVITY [J].
GAREGG, PJ ;
HULTBERG, H .
CARBOHYDRATE RESEARCH, 1981, 93 (01) :C10-C11
[7]   REGIOSELECTIVE REDUCTIVE RING-OPENING OF 4-METHOXYBENZYLIDENE ACETALS OF HEXOPYRANOSIDES - ACCESS TO A NOVEL PROTECTING-GROUP STRATEGY .1. [J].
JOHANSSON, R ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (10) :2371-2374
[8]   IMMUNOCHEMICAL STUDIES ON BLOOD GROUPS .7. CHEMICAL CHANGES ASSOCIATED WITH DESTRUCTION OF BLOOD GROUP ACTIVITY AND ENHANCEMENT OF THE TYPE-XIV CROSS-REACTIVITY BY PARTIAL HYDROLYSIS OF HOG AND HUMAN BLOOD GROUP-A, GROUP-B, AND O SUBSTANCES [J].
KABAT, EA ;
BAER, H ;
BEZER, AE ;
KNAUB, V .
JOURNAL OF EXPERIMENTAL MEDICINE, 1948, 88 (01) :43-57
[9]   ACCEPTOR SUBSTRATE RECOGNITION BY N-ACETYLGLUCOSAMINYLTRANSFERASE-V - CRITICAL ROLE OF THE 4''-HYDROXYL GROUP IN BETA-D-GLCPNAC-(1-)2)-ALPHA-D-MANP(1-)6)-BETA-D-GLCP-OR [J].
KANIE, O ;
CRAWLEY, SC ;
PALCIC, MM ;
HINDSGAUL, O .
CARBOHYDRATE RESEARCH, 1993, 243 (01) :139-164
[10]   SOME 2,3,4,6-TETRA-O-(PARA-CHLOROBENZYL)-ALPHA-D-HEXOPYRANOSES [J].
KOTO, S ;
INADA, S ;
MORISHIMA, N ;
ZEN, S .
CARBOHYDRATE RESEARCH, 1980, 87 (02) :294-296