Carbohydrate Research 2007-11-05

First synthesis of tepidopterin [2'-O-(2-acetamido-2-deoxy-beta-d-glucopyranosyl)-L-threo-biopterin].

Tadashi Hanaya, Hiroki Baba, Hiroshi Yamamoto

Index: Carbohydr. Res. 342(15) , 2159-62, (2007)

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Abstract

N(2)-(N,N-Dimethylaminomethylene)-1'-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-threo-biopterin (14) was prepared from L-xylose in an 11-step-sequence. The first synthesis of tepidopterin (3) was achieved by treatment of 14 with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups.