TY - JOUR
T1 - An efficient synthesis of 2′-O-(β-d-glucopyranosyl)- and 2′-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-l-biopterins
AU - Hanaya, Tadashi
AU - Soranaka, Kazuyuki
AU - Harada, Koichiro
AU - Yamaguchi, Hiroshi
AU - Suzuki, Ryo
AU - Endo, Yusumi
AU - Yamamoto, Hiroshi
AU - Pfleiderer, Wolfgang
PY - 2006/1/1
Y1 - 2006/1/1
N2 - 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 trichloroacetimidate (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).
AB - 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 trichloroacetimidate (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).
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U2 - 10.3987/COM-05-S(T)28
DO - 10.3987/COM-05-S(T)28
M3 - Article
AN - SCOPUS:33646883040
SN - 0385-5414
VL - 67
SP - 299
EP - 310
JO - Heterocycles
JF - Heterocycles
IS - 1
ER -