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Volumn 33, Issue 7, 1992, Pages 907-910

A short, stereospecific synthesis of dihydrooxazoles from serine and threonine derivatives

Author keywords

[No Author keywords available]

Indexed keywords

OXAZOLE DERIVATIVE;

EID: 0026604531     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)91572-7     Document Type: Article
Times cited : (197)

References (39)
  • 31
    • 0011809975 scopus 로고
    • Studies on 2-aziridinecarboxylic acid. V. Formation of dehydroamino acid containing peptides via the isomerization by NaI of 2-aziridinecarboxylic acid containing peptides.
    • 2≠H are reported to eliminate rather than to expand to five-membered heterocycles;see, for example
    • (1982) Bulletin of the Chemical Society of Japan , vol.55 , pp. 174
    • Okawa1    Nakajima2    Tanaka3    Neya4
  • 37
    • 84918672775 scopus 로고    scopus 로고
    • Hydroxy amides were synthesized by dicyclohexylcarbodiimide (DCC) or N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (EDCI) coupling of the N-Cbz-protected amino acid with the appropriate amino ester or methyl amide in THF.
  • 38
    • 84918702098 scopus 로고    scopus 로고
    • D) compounds.
  • 39
    • 84918704636 scopus 로고    scopus 로고
    • A typical protocol for the cyclization with Burgess reagent is as follows: A solution of 0.16 mmol of the dipeptide in 3 mL of dry THF in a Pyrex tube was flushed with nitrogen and 0.176 mmol (1.1 eq.) of the Burgess reagent was added in small portions. The tube was capped, and the reaction mixture was heated at 70°C in an oil bath for 0.7–2.5 h. The solution was allowed to cool to room temperature and evaporated onto silica gel. Chromatographic purification of the residue led to the isolation of the desired 4,5-dihydrooxazoles in 62–85% yield.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.