TY - JOUR
T1 - First synthesis of a natural isoxanthopterin glycoside, asperopterin-A
AU - Hanaya, Tadashi
AU - Ejiri, Kazumasa
AU - Yamamoto, Hiroshi
N1 - Copyright:
Copyright 2012 Elsevier B.V., All rights reserved.
PY - 2012
Y1 - 2012
N2 - The key precursor, N 2-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.
AB - The key precursor, N 2-(N,N-dimethylaminomethylene)-6- hydroxymethyl- 8-methyl-3-[2-(4-nitrophenyl)ethyl]-7-xanthopterin (9) was efficiently prepared from 2,5-diamino-6-methylamino-3H-pyrimidin-4-one (3) and ethyl 3-(tert-butyldimethylsilyloxy)-2-oxopropionate (11). The first synthesis of asperopterin-A (2b) was achieved by treatment of 9 with 1-O-acetyl-2,3,5- tri-O-benzoyl-β-D-ribofuranose (15) in the presence of tin(IV) chloride, followed by removal of the protecting groups.
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U2 - 10.3987/COM-11-S(P)57
DO - 10.3987/COM-11-S(P)57
M3 - Article
AN - SCOPUS:84856551388
VL - 84
SP - 801
EP - 813
JO - Heterocycles
JF - Heterocycles
SN - 0385-5414
IS - 2
ER -