Abstract
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).
| Original language | English |
|---|---|
| Pages (from-to) | 1-7 |
| Number of pages | 7 |
| Journal | Pteridines |
| Volume | 6 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 1995 |
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Keywords
- Biopterin 3-Methyl-L-biopterin 04-Methyl-L-biopterin Selective alkylation Selective protection N2
- N(3)-Protected-L-biopterin N
- N-Dimethylaminomethylene p-Nitrophenethyl Selective deprotection Synthesis Pteridines
ASJC Scopus subject areas
- Biochemistry
- Clinical Biochemistry
- Molecular Medicine
Cite this
Pteridines CV : 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. / Hanaya, Tadashi; Torigoe, Kiyoshi; Soranaka, Kazuyuki; Yamamoto, Horoshi; Qizheng, Yao; Pfleiderer, Wolfgang.
In: Pteridines, Vol. 6, No. 1, 1995, p. 1-7.Research output: Contribution to journal › Article
}
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
PY - 1995
Y1 - 1995
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
UR - http://www.scopus.com/inward/record.url?scp=0028927042&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0028927042&partnerID=8YFLogxK
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 -