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Paper | Special issue | Vol 67, No. 1, 2006, pp.299-310
Published online, 26th August, 2005
DOI: 10.3987/COM-05-S(T)28
An Efficient Synthesis of 2’-O-(β-D-Glucopyranosyl)- and 2’-O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-L-biopterins

Tadashi Hanaya,* Kazuyuki Soranaka, Koichiro Harada, Hiroshi Yamaguchi, Ryo Suzuki, Yusumi Endo, Hiroshi Yamamoto, and Wolfgang Pfleiderer

*Department of Chemistry, Faculty of Science, Okayama University, 3-1-1 Tsushima-naka, Okayama 700-8530, Japan

Abstract

N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]-1’,2’-di-O-trimethylsilyl-L-biopterin (6) was prepared from L-biopterin in 5 steps. Glycosylation of 6 with 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranosyl trichloro-acetimidate (9) and 1,3,4,6-tetra-O-acetyl-2-phtalimido-β-D-glucopyranose (10) respectively afforded the corresponding 2’-O-(β-D-glucopyranosyl) derivatives (12b, 12c) as major products. Removal of protecting groups of 12c provided naturally occurring limipterin (2).