TY - JOUR
T1 - Pteridines CV
T2 - Selective n(3)-and 04-Alkylation of L-Biopterin: A Convenient Synthesis of 3-and 04-Methyl-L-Biopterin and the Versatile N2-(N,N-dimethylami-nomethylene)-N(3)-p-nitrophenethyl-Protected L-Biopterin
AU - Hanaya, Tadashi
AU - Torigoe, Kiyoshi
AU - Soranaka, Kazuyuki
AU - Yamamoto, Horoshi
AU - Qizheng, Yao
AU - Pfleiderer, Wolfgang
N1 - Funding Information:
We are grateful to Kanegafuchi Chemical Co. Ltd. (Osaka) for the supply of hiopterin to us. The present work was partially supported hy a Grant-in-Aid for Scientific Research No. 03045035 from the Japanese Ministry of Education. Science and Culture.
PY - 1995/2
Y1 - 1995/2
N2 - Treatment of L-biopterin (1) with N, N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1,2-di-0-acetyl-N:2-(N, N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl derivatives (7). The protective groups on the side chain diols and N of these compounds were selectively cleaved to furnish products 6, 8-10 among which 9 is naturally occurring 3-methyl-L-biopterin and 8 is N2:,N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2::1,2'-0-acetyl-L-biopterin (11) afforded 04-methyl (12) and 04-NPE derivatives (13), both of which yielded 04-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18).
AB - Treatment of L-biopterin (1) with N, N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1,2-di-0-acetyl-N:2-(N, N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl derivatives (7). The protective groups on the side chain diols and N of these compounds were selectively cleaved to furnish products 6, 8-10 among which 9 is naturally occurring 3-methyl-L-biopterin and 8 is N2:,N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2::1,2'-0-acetyl-L-biopterin (11) afforded 04-methyl (12) and 04-NPE derivatives (13), both of which yielded 04-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18).
KW - Biopterin 3-Methyl-L-biopterin 04-Methyl-L-biopterin Selective alkylation Selective protection N2
KW - N(3)-Protected-L-biopterin N
KW - N-Dimethylaminomethylene p-Nitrophenethyl Selective deprotection Synthesis Pteridines
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U2 - 10.1515/pteridines.1995.6.1.1
DO - 10.1515/pteridines.1995.6.1.1
M3 - Article
AN - SCOPUS:0028927042
VL - 6
SP - 1
EP - 7
JO - Pteridines
JF - Pteridines
SN - 0933-4807
IS - 1
ER -