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Communication | Special issue | Vol 77, No. 2, 2009, pp.747-753
Published online, 9th September, 2008
DOI: 10.3987/COM-08-S(F)60
First Synthesis of Biopterin α-D-Glucoside

Tadashi Hanaya,* Hiroki Baba, and Hiroshi Yamamoto

*Graduate School of Natural Science and Technology, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

A novel glycosyl donor, 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-D-glucopyranosy bromide (15) was efficiently prepared from D-glucose in 8 steps. The first synthesis of 2’-O-(α-D-glucopyranosyl)biopterin (2) was achieved by treatment of the key precursor, N2-(N,N-dimethylaminomethylene)-1’-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (6) with 15 in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.