1237730-23-2Relevant academic research and scientific papers
Synthesis of a mannose hexasaccharide related to the cell wall mannan of candida dubliniensis and trychophyton mentagrophytes
Zong, Guanghui,Yu, Naili,Xu, Yanjun,Zhang, Jianjun,Wang, Daoquan,Liang, Xiaomei
experimental part, p. 1666 - 1672 (2010/06/22)
2,6-Branched mannose hexasaccharide 1 related to the cell wall polysaccharide of Candida dubliniensis and Trychophyton mentagrophytes was concisely synthesized from 4-methoxyphenyl -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 1C NMR, MS, HRMS, and elemental analysis. Georg Thieme Verlag Stuttgart - New York.
