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Volumn 69, Issue 25, 2004, Pages 8694-8701

A total synthesis of hydroxylysine in protected form and investigations of the reductive opening of p-methoxybenzylidene acetals

Author keywords

[No Author keywords available]

Indexed keywords

ALKYLATION; AMINES; BENZENE; CARBOXYLIC ACIDS; CHELATION; REDUCTION;

EID: 10044286150     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049136w     Document Type: Article
Times cited : (20)

References (43)
  • 19
    • 10044234778 scopus 로고    scopus 로고
    • note
    • D +26 (c 1.0, MeOH) [lit. +26 (c 1.0, MeOH, Sigma-Aldrich)].
  • 37
    • 10044282427 scopus 로고    scopus 로고
    • note
    • Compound 11 was epimerized at the stereogenic center corresponding to Cα in hydroxylysine by treatment with NaHMDS (1 equiv) in THF. Analysis of the diasteromeric mixture by reversed-phase HPLC displayed two peaks having identical mass spectra. Only one of the two diastereomers was detected by HPLC when 11 was prepared by alkylation of 16b with 10.
  • 41
    • 10044256109 scopus 로고    scopus 로고
    • note
    • Two equivalents of sodium cyanoborohydride and tert-butyldimethyl silyl chloride was used with acetonitrile as solvent at room temperature.
  • 42
    • 10044245665 scopus 로고    scopus 로고
    • note
    • 1H NMR shift of ∼1.15 ppm for the proximal hydrogen atom. As expected acetylation of the primary hydroxyl group in 20a/b caused a smaller shift (∼0.35 ppm) of the adjacent hydrogen atoms. The identity and the yields for compounds 22a/b, 23a/b, 26a/b, and 27a/b obtained after reductive opening of 21 and 25 were determined in the same manner.
  • 43
    • 10044250772 scopus 로고    scopus 로고
    • note
    • 13C NMR data.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.