TY - JOUR
T1 - Synthetic studies on pterin glycosides
T2 - the first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin
AU - Hanaya, Tadashi
AU - Baba, Hiroki
AU - Toyota, Hiroki
AU - Yamamoto, Hiroshi
N1 - Funding Information:
We are grateful to the SC-NMR Laboratory of Okayama University for the NMR measurements and to WESCO Scientific Promotion Foundation (to T.H.), which partially supported this work.
PY - 2009/9/19
Y1 - 2009/9/19
N2 - l-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.
AB - l-Rhamnose was led, in a 14-step-sequence, to N2-(N,N-dimethylaminomethylene)-1′-O-(4-methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]biopterin (23), an appropriately protected precursor for 2′-O-glycosylation, while 4,6-di-O-acetyl-2,3-di-O-(4-methoxybenzyl)-α-d-glucopyranosyl bromide (32), a novel glycosyl donor, was efficiently prepared from d-glucose in 8 steps. The first synthesis of 2′-O-(α-d-glucopyranosyl)biopterin (2a) was achieved by treatment of the key intermediate 23 with 32 in the presence of silver triflate and tetramethylurea, followed by successive removal of the protecting groups.
KW - Glycosylation
KW - Protecting group
KW - Pteridine
KW - Pterin glycoside
KW - Total synthesis
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U2 - 10.1016/j.tet.2009.07.043
DO - 10.1016/j.tet.2009.07.043
M3 - Article
AN - SCOPUS:68549101675
SN - 0040-4020
VL - 65
SP - 7989
EP - 7997
JO - Tetrahedron
JF - Tetrahedron
IS - 38
ER -