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Paper | Special issue | Vol 95, No. 1, 2017, pp.390-409
Published online, 19th December, 2016
DOI: 10.3987/COM-16-S(S)32
Efficient Total Syntheses of Natural Neopterin Glycosides: Neopterin Glucronide and Solfapterin

Tadashi Hanaya,* Katsuya Iwasaki, Kaori Saeki, and Takafumi Hattori

*Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Okayama 700-8530, Japan

Abstract

1’,2’-Di-O-acetyl-N2-(N,N-dimethylaminomethylene)-3-[2-(4-nitro- phenyl)ethyl]neopterin (11a) and its 1’,2’-di-O-benzoyl analog (11b) were prepared from neopterin in 5 steps, respectively. Glycosylation of 11a with methyl 2,3,4-tri-O-benzoyl-α-D-glucopyranosyluronate bromide (15b) in the presence of silver triflate afforded the corresponding 3’-O-(β-D-gluco- pyranosyl)neopterin derivative (18) in 64% yield. The similar treatment of 11b with 2-azido-3,4,6-tri-O-benzoyl-2-deoxy-α-D-glucopyranosyl bromide (21b) provided the corresponding 3’-O-(α-D-glucopyranosyl)neopterin derivative (23a) in 58% yield. The first syntheses of neopterin glucronide (5) and solfapterin (6) were achieved by successive removal of the protecting groups of 18 and 23a, respectively.