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

Tadashi Hanaya, Kiyoshi Torigoe, Kazuyuki Soranaka, Horoshi Yamamoto, Yao Qizheng, Wolfgang Pfleiderer

Research output: Contribution to journalArticle

19 Citations (Scopus)

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 languageEnglish
Pages (from-to)1-7
Number of pages7
JournalPteridines
Volume6
Issue number1
DOIs
Publication statusPublished - 1995

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Biopterin
Pteridines
Alkylation
Derivatives
Acetals

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 journalArticle

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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).",
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