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Short Paper | Regular issue | Vol 89, No. 3, 2014, pp.763-774
Published online, 6th February, 2014
DOI: 10.3987/COM-14-12944
Synthesis of a Phosphatidylinositol Dimannoside Using 2-(Azidomethyl)benzoate Mannosyl Donors

Shuichi Ohira, Yoshiki Yamaguchi, Takashi Takahashi, and Hiroshi Tanaka*

*Department of Applied Chemistry, Graduate School of Science and Technology, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan

Abstract

We report on the synthesis of an acyl phosphatidylinositol dimannoside using the 2-(azidomethyl)benzoate-protected mannosyl donors. An equatorial-orientated C6 hydroxyl group in inositol exhibited higher reactivity towards glycosylation than the axial-orientated C2 hydroxyl group. Sequential glycosylation of the C6 and C2 hydroxyls with two different thioglycosides allowed the synthesis of a 2,6-di-O-α-mannosyl inositol in one-pot. After incorporation of a fatty acid and an acyl phosphatidyl moiety, all protecting groups involving benzyl ethers, benzylidene acetal and the 2-(azidomethyl)benzoate were removed under hydrogenolysis to provide an acyl phosphatidylinositol dimannoside.