First synthesis of tepidopterin [2'-O-(2-acetamido-2-deoxy-beta-d-glucopyranosyl)-L-threo-biopterin].
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.
Hanaya
Tadashi
T
Department of Chemistry, Faculty of Science, Okayama University, Tsushima-naka, Okayama 700-8530, Japan. hanaya@cc.okayama-u.ac.jp
Baba
Hiroki
H
Yamamoto
Hiroshi
H
D001708:Biopterins / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001965:Bromides / Q000737:chemistry; D002236:Carbohydrate Conformation; D002241:Carbohydrates / Q000737:chemistry; D006027:Glycosides / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008698:Mesylates / Q000737:chemistry; D008782:Methylurea Compounds / Q000737:chemistry; D008956:Models, Chemical; D009844:Oligosaccharides / Q000737:chemistry; D011522:Protons; D011622:Pterins / Q000737:chemistry*; D014994:Xylose / Q000737:chemistry
D001965:Bromides; D002241:Carbohydrates; D006027:Glycosides; D008698:Mesylates; D008782:Methylurea Compounds; D009844:Oligosaccharides; D011522:Protons; D011622:Pterins; C110868:tepidopterin; D001708:Biopterins; C004168:1,1,3,3-tetramethylurea; D014994:Xylose; C012077:trifluoromethanesulfonic acid