Hanaya, Tadashi Department of Chemistry, Faculty of Science, Okayama University
Baba, Hiroki Department of Chemistry, Faculty of Science, Okayama University
Toyota, Hiroki Department of Chemistry, Faculty of Science, Okayama University
Yamamoto, Hiroshi School of Pharmacy, Shujitsu University
L-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.
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