TY - JOUR
T1 - An efficient synthesis of 2′-O-(β-D-ribofuranosyl)biopterin
AU - Hanaya, Tadashi
AU - Torigoe, Kiyoshi
AU - Soranaka, Kazuyuki
AU - Fujita, Hiroshi
AU - Yamamoto, Hiroshi
AU - Pfleiderer, Wolfgang
PY - 2008/9
Y1 - 2008/9
N2 - N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.
AB - N2-(N,N-Dimethylaminomethylene)-3-[2-(4-nitrophenyl)ethyl]- 1′,2′-di-O-(trimethylsilyl)biopterin (4) was prepared from biopterin (1a, 86% overall yield) in 5 steps. Glycosylation of 4 with 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose (5a) and its 2,3,5-tri-O-benzoyl analog (5b) respectively afforded the corresponding 2′-O-(2,3,5-tri-O- acetyl-and 2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)biopterin derivatives (6a, 42% and 6b, 60%) as major products. Removal of the protecting groups of 6b provided 2′-O-(β-D-ribofuranosyl)biopterin (1c, 87% overall yield) in 3 steps.
KW - Biopterin D-riboside
KW - Glycosylation
KW - Protecting groups
KW - Pterin glycoside
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U2 - 10.1515/pteridines.2008.19.1.72
DO - 10.1515/pteridines.2008.19.1.72
M3 - Article
AN - SCOPUS:55449129393
SN - 0933-4807
VL - 19
SP - 72
EP - 78
JO - Pteridines
JF - Pteridines
IS - 3
ER -