TY - JOUR
T1 - Novel preparation of a 2′-O-acetyl-1′-O-(4-methoxybenzyl)-L- biopterin derivative, a versatile precursor for a selective synthesis of L-biopterin glycosides
AU - Hanaya, Tadashi
AU - Toyota, Hiroki
AU - Yamamoto, Hiroshi
PY - 2006/8/17
Y1 - 2006/8/17
N2 - L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.
AB - L-Rhamnose was converted, over a 13-step-sequence, into 2′-O-acetyl-N2-(N,N-dimethylaminomethylene)-1′-O-(4- methoxybenzyl)-3-[2-(4-nitrophenyl)ethyl]-L-biopterin, an appropriately protected precursor of 1′-O- and 2′-O-monoglycosyl-L-biopterin. Thus, the first selective synthesis of these L-biopterin glycosides was accomplished by treatment of the precursor with either DDQ or sodium methoxide, then with tetra-O-benzoyl-α-D-glucopyranosyl bromide in the presence of silver triflate and tetramethylurea, followed by removal of the remaining protecting groups.
KW - Glycosylations
KW - L-biopterin glycosides
KW - Limipterin
KW - Protecting groups
KW - Pteridine
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U2 - 10.1055/s-2006-949620
DO - 10.1055/s-2006-949620
M3 - Article
AN - SCOPUS:33748286171
SP - 2075
EP - 2078
JO - Synlett
JF - Synlett
SN - 0936-5214
IS - 13
ER -