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Synthesis 2010(10): 1666-1672  
DOI: 10.1055/s-0029-1218719
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Mannose Hexasaccharide Related to the Cell Wall Mannan of Candida dubliniensis and Trychophyton mentagrophytes

Guanghui Zong, Naili Yu, Yanjun Xu, Jianjun Zhang*, Daoquan Wang, Xiaomei Liang*
Key Laboratory of Pesticide Chemistry and Application Technology, Department of Applied Chemistry, China Agricultural University, Beijing 100193, P. R. of China
Fax: +86(10)62732219; e-Mail: zhangjianjun@cau.edu.cn; e-Mail: nmrlab@cau.edu.cn;
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Received 14 January 2010
Publikationsdatum:
26. März 2010 (online)

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Abstract

2,6-Branched mannose hexasaccharide 1 related to the cell wall polysaccharide of Candida dubliniensis and Trychophyton mentagrophytes was concisely synthesized from 4-methoxyphenyl α-d-mannopyranoside (6) in 11 steps in 26% total yield. The efficiency of the synthesis relies on the preparation of a trisaccharide acceptor 2 with three free hydroxy groups, which could be glycosylated with trichloroacetimidate 19 to provide the protected hexasaccharide 20 in one step. Compound 2 was obtained via sequential assembly from the building blocks, 2,6-di-O-allyloxycarbonyl-3,4-di-O-benzoyl-α-d-mannopyranose trichloroacetimidate (3), 4-methoxyphenyl 3,4-di-O-benzoyl-α-d-mannopyranoside (4), and 4-methoxyphenyl 4-O-acetyl-3-O-benzoyl-α-d-mannopyranoside (5). Structures of target compound and intermediates were characterized by ¹H and ¹³C NMR, MS, HRMS, and elemental analysis.

Key words

synthesis - oligosaccharide - mannose - Candida dubliniensis - Trychophyton mentagrophytes