TY - JOUR
T1 - Efficient total syntheses of natural pterin glycosides
T2 - limipterin and tepidopterin
AU - Hanaya, Tadashi
AU - Baba, Hiroki
AU - Toyota, Hiroki
AU - Yamamoto, Hiroshi
PY - 2008/2/25
Y1 - 2008/2/25
N2 - The key, versatile precursors N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from d-xylose (in 14 steps) and l-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.
AB - The key, versatile precursors N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (29a) and its ciliapterin analog (29b) were prepared, respectively, from d-xylose (in 14 steps) and l-xylose (in 11 steps). Treatment of 29a and 29b with 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-d-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the protecting groups, led to the first selective syntheses of limipterin (3) and tepidopterin (5), respectively.
KW - Glycosylation
KW - Protecting group
KW - Pteridine
KW - Pterin glycoside
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U2 - 10.1016/j.tet.2007.12.042
DO - 10.1016/j.tet.2007.12.042
M3 - Article
AN - SCOPUS:38349095041
SN - 0040-4020
VL - 64
SP - 2090
EP - 2100
JO - Tetrahedron
JF - Tetrahedron
IS - 9
ER -