Pteridines CV
Treatment of L-biopterin (I) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N'-(N,N-dimethylaminomethylene)-L-biopterin (4), which was converted by the Mitsunobu reaction into 3-methyl (5) and 3-p-nitrophenetyl...
| Main Authors: | , , , , , |
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| Format: | Article |
| Language: | English |
| Published: |
De Gruyter
1995-02-01
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| Series: | Pteridines |
| Subjects: | |
| Online Access: | https://doi.org/10.1515/pteridines.1995.6.1.1 |
| _version_ | 1818718329558269952 |
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| author | Hanaya Tadashi Torigoe Kiyoshi Soranaka Kazuyuki Yamamoto Horoshi Qizhengt Yao Pfleiderer Wolfgang |
| author_facet | Hanaya Tadashi Torigoe Kiyoshi Soranaka Kazuyuki Yamamoto Horoshi Qizhengt Yao Pfleiderer Wolfgang |
| author_sort | Hanaya Tadashi |
| collection | DOAJ |
| description | Treatment of L-biopterin (I) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N'-(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 N2 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 N',N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2:I',2'-0-acetyl-L-biopterin (II) afforded 04-methyl (12) and 04-NPE derivatives (13), both of which yielded 0 4-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18). |
| first_indexed | 2024-12-17T19:49:19Z |
| format | Article |
| id | doaj.art-818816b99f5d45ef8bcdce0eb2e25953 |
| institution | Directory Open Access Journal |
| issn | 0933-4807 2195-4720 |
| language | English |
| last_indexed | 2024-12-17T19:49:19Z |
| publishDate | 1995-02-01 |
| publisher | De Gruyter |
| record_format | Article |
| series | Pteridines |
| spelling | doaj.art-818816b99f5d45ef8bcdce0eb2e259532022-12-21T21:34:46ZengDe GruyterPteridines0933-48072195-47201995-02-01611710.1515/pteridines.1995.6.1.1Pteridines CVHanaya Tadashi0Torigoe Kiyoshi1Soranaka Kazuyuki2Yamamoto Horoshi3Qizhengt Yao4Pfleiderer Wolfgang5Department of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700, JapanDepartment of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700, JapanDepartment of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700, JapanDepartment of Chemistry, Faculty of Science, Okayama University, Tsushima, Okayama 700, JapanFakultät für Chemie, Universität Konstanz, Postfach 5560, 0-78434 Konstanz, GermanyFakultät für Chemie, Universität Konstanz, Postfach 5560, 0-78434 Konstanz, GermanyTreatment of L-biopterin (I) with N,N-dimethyformamide dimethyl- (or diethyl)acetal and then with acetic anhydride in pyridine gave 1',2'-di-O-acetyl-N'-(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 N2 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 N',N(3)-protected biopterin, a versatile intermediate for various reactions on the side-chain diol. In contrast, the same Mitsunobu reactions of tri-N2:I',2'-0-acetyl-L-biopterin (II) afforded 04-methyl (12) and 04-NPE derivatives (13), both of which yielded 0 4-methyl-L-biopterin (14) and subsequently led to 4-amino-L-biopterin (18).https://doi.org/10.1515/pteridines.1995.6.1.1biopterin3-methyl-l-biopterin04-methyl-l-biopterinselective alkylationselective protectionn2,n(3)-protected-l-biopterinn,n-dimethylaminomethylenep-nitrophenethylselective deprotectionsynthesispteridines |
| spellingShingle | Hanaya Tadashi Torigoe Kiyoshi Soranaka Kazuyuki Yamamoto Horoshi Qizhengt Yao Pfleiderer Wolfgang Pteridines CV Pteridines 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 |
| title | Pteridines CV |
| title_full | Pteridines CV |
| title_fullStr | Pteridines CV |
| title_full_unstemmed | Pteridines CV |
| title_short | Pteridines CV |
| title_sort | pteridines cv |
| topic | 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 |
| url | https://doi.org/10.1515/pteridines.1995.6.1.1 |
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