Novel regio- and stereoselective synthesis of 6-substituted pteridines and naturally occurring L-erythro-biopterin

S. Murata, T. Sugimoto, S. Ogiwara, Koichi Mogi, H. Wasada

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

Condensation of 2,4,5-triamino-6-butoxypyrimidine with various 2-formyloxiranes followed by oxidation with iodine affords 2-amino-4-butoxy-6-(1-hydroxyalkyl)pteridines regioselectively. Naturally occurring L-erythro-biopterin is synthesized from (1S,2S,3S)-2-formyl-3-(1-hydroxyethyl)oxirane. The reaction proceeds via 5,6-dihydropteridine, and the mechanism is discussed with the help of molecular orbital calculations.

Original languageEnglish
Pages (from-to)303-308
Number of pages6
JournalSynthesis
Issue number3
Publication statusPublished - 1992
Externally publishedYes

Fingerprint

Biopterin
Pteridines
Ethylene Oxide
Orbital calculations
Molecular orbitals
Iodine
Condensation
Oxidation

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

Novel regio- and stereoselective synthesis of 6-substituted pteridines and naturally occurring L-erythro-biopterin. / Murata, S.; Sugimoto, T.; Ogiwara, S.; Mogi, Koichi; Wasada, H.

In: Synthesis, No. 3, 1992, p. 303-308.

Research output: Contribution to journalArticle

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AU - Mogi, Koichi

AU - Wasada, H.

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