Improved iterative olefination approach to oligosaccharide mimics:: stereoselective synthesis of β-(1→6)-D-galactopentaose methylene isostere

被引:17
作者
Dondoni, A [1 ]
Mizuno, M [1 ]
Marra, A [1 ]
机构
[1] Univ Ferrara, Dipartmento Chim, Chim Organ Lab, I-44100 Ferrara, Italy
关键词
glycomimetics; glycosidase inhibitors; oligosaccharide isosteres; Wittig reaction;
D O I
10.1016/S0040-4039(00)01112-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The title C-pentagalactoside featuring beta-(1-->6) ethylene bridges between the D-galactopyranose units has been prepared through four consecutive cycles comprising the Wittig reaction of a formyl C-galactoside building block with sugar phosphorane substrate followed by the introduction of a methylphosphonium group at the nonreducing end; the target product was obtained by hydrogenolysis of the tetraene pentasaccharide. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:6657 / 6660
页数:4
相关论文
共 23 条
[1]  
Andersen L, 1998, SYNLETT, P1393
[2]   Synthesis of a versatile neuraminic acid "C"-disaccharide precursor for the synthesis of C-glycoside analogues of gangliosides [J].
Bazin, HG ;
Du, YG ;
Polat, T ;
Linhardt, RJ .
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7254-7259
[3]   Synthesis of alpha- and beta-D-(1->-6)-C-disaccharides by Wittig olefination of formyl C-glycosides with glycopyranose 6-phosphoranes [J].
Dondoni, A ;
Zuurmond, HM ;
Boscarato, A .
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (23) :8114-8124
[4]   Synthesis of (1→6)-C-oligogalactosides by iterative Wittig olefination [J].
Dondoni, A ;
Kleban, M ;
Zuurmond, H ;
Marra, A .
TETRAHEDRON LETTERS, 1998, 39 (43) :7991-7994
[5]   Glycobiology: Toward understanding the function of sugars [J].
Dwek, RA .
CHEMICAL REVIEWS, 1996, 96 (02) :683-720
[6]   MAPPING OF SUBSITES OF MONOCLONAL, ANTI-CARBOHYDRATE ANTIBODIES USING DEOXY AND DEOXYFLUORO SUGARS [J].
GLAUDEMANS, CPJ .
CHEMICAL REVIEWS, 1991, 91 (01) :25-33
[7]  
Griffin FK, 1999, ANGEW CHEM INT EDIT, V38, P2939, DOI 10.1002/(SICI)1521-3773(19991004)38:19<2939::AID-ANIE2939>3.0.CO
[8]  
2-S
[9]   PREFERRED CONFORMATION OF C-GLYCOSIDES .10. SYNTHESIS AND CONFORMATIONAL-ANALYSIS OF CARBON TRISACCHARIDES [J].
HANEDA, T ;
GOEKJIAN, PG ;
KIM, SH ;
KISHI, Y .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (02) :490-498
[10]  
Jarreton O, 1999, CHEM-EUR J, V5, P430, DOI 10.1002/(SICI)1521-3765(19990201)5:2<430::AID-CHEM430>3.0.CO