Synthesis of heparin oligosaccharides

被引:134
作者
Lee, JC
Lu, XA
Kulkarni, SS
Wen, YS
Hung, SC [1 ]
机构
[1] Acad Sinica, Inst Chem, Taipei 115, Taiwan
[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu 300, Taiwan
关键词
D O I
10.1021/ja038244h
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-β-l-idopyranose from commercially available diacetone α-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out. Copyright © 2004 American Chemical Society.
引用
收藏
页码:476 / 477
页数:2
相关论文
共 23 条
[1]   RE-EXAMINATION OF THE ACID-HYDROLYSIS OF 5,6-ANHYDRO-1,2-O-ISOPROPYLIDENE-BETA-L-IDOFURANOSE [J].
BAGGETT, N ;
SAMRA, AK .
CARBOHYDRATE RESEARCH, 1984, 127 (01) :149-153
[2]  
Capila I, 2002, ANGEW CHEM INT EDIT, V41, P391
[3]   Dengue virus infectivity depends on envelope protein binding to target cell heparan sulfate [J].
Chen, YP ;
Maguire, T ;
Hileman, RE ;
Fromm, JR ;
Esko, JD ;
Linhardt, RJ ;
Marks, RM .
NATURE MEDICINE, 1997, 3 (08) :866-871
[4]  
Conrad H.E., 1998, HEPARIN BINDING PROT
[5]  
de Paz JL, 2001, CHEMBIOCHEM, V2, P673, DOI 10.1002/1439-7633(20010903)2:9<673::AID-CBIC673>3.0.CO
[6]  
2-7
[7]   SPECIFICITY STUDIES ON THE HEPARIN LYASES FROM FLAVOBACTERIUM-HEPARINUM [J].
DESAI, UR ;
WANG, HM ;
LINHARDT, RJ .
BIOCHEMISTRY, 1993, 32 (32) :8140-8145
[8]   Heparin structure and interactions with basic fibroblast growth factor [J].
Faham, S ;
Hileman, RE ;
Fromm, JR ;
Linhardt, RJ ;
Rees, DC .
SCIENCE, 1996, 271 (5252) :1116-1120
[9]   A facile chemoselective deacetylation in the presence of benzoyl and p-bromobenzoyl groups using p-toluenesulfonic acid [J].
González, AG ;
Brouard, I ;
León, F ;
Padrón, JI ;
Bermejo, J .
TETRAHEDRON LETTERS, 2001, 42 (18) :3187-3188
[10]   1,6-anhydro-β-L-hexopyranoses as potent synthons in the synthesis of the disaccharide units of bleomycin A2 and heparin [J].
Hung, SC ;
Thopate, SR ;
Chi, FC ;
Chang, SW ;
Lee, JC ;
Wang, CC ;
Wen, YS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (13) :3153-3154