Convergent synthesis of a galactofuranosylated mannan, the repeating unit of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467

被引:3
|
作者
Ma, ZC [1 ]
Zhang, JJ [1 ]
Kong, FZ [1 ]
机构
[1] Acad Sinica, Ecoenvironm Sci Res Ctr, Beijing 100085, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetasy.2004.03.041
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
An undecasaccharide repeating unit of the polysaccharide of Trichophyton mentagrophytes IFO 5466 and Trichophyton rubrum IFO 5467, alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-alpha-D-Manp(1 --> 2)-alpha-D-Manp-(1 --> 2)-alpha-D-Manp-(1 --> 6)-alpha-D-Manp-(1 --> 2)-[beta-D-Galf-(1 --> 3)]-Manp was synthesized as its allyl glycoside by coupling of a octasaccharide trichloroacetimidate donor 19 with a trisaccharide acceptor 28. The donor 19 and 28 were obtained with allyl 3-O-acetyl-2-O-betizoyl-alpha-D-mannopyranoside 2, allyl 3-O-acetyl-4,6-di-O-benzoyl-alpha-D-mannopyranoside 9, allyl 3,4,6-tri-O-benzoyl-alpha-D-mannopyranosyl-(1 --> 2)-3,4,6-tri-O-belizoyl-alpha-D-mannopyranoside 13, 6-O-acetyl-2,3,4-tri-O-benzoyl-alpha-D-mannopyranosyl trichloroacetimidate 26 and 2,3,5,6-tetra-O-benzoyl-beta-D-galactofuraliosyl trichloroacetimidate 16 as the key synthons by appropriate combination through simple transformation. (C) 2004 Elsevier Ltd. All rights reserved.
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页码:1517 / 1525
页数:9
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