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Volumn 41, Issue 16, 2000, Pages 2765-2768

Efficient enantioselective syntheses of chloramphenicol and (D)-threo- and (D)-erythro-sphingosine

Author keywords

[No Author keywords available]

Indexed keywords

CHLORAMPHENICOL; SPHINGOSINE DERIVATIVE;

EID: 0034655861     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00301-4     Document Type: Article
Times cited : (34)

References (38)
  • 7
    • 0003435820 scopus 로고
    • (b) Merck and Co.: Rahway, NJ
    • (b) Merck Index; 10th ed.; Merck and Co.: Rahway, NJ, 1983; p. 289.
    • (1983) Merck Index; 10th Ed. , pp. 289
  • 13
    • 1542499011 scopus 로고
    • 2H, THF) followed by alkaline hydrolysis (2N KOH, EtOH, reflux). See: (a)
    • 2H, THF) followed by alkaline hydrolysis (2N KOH, EtOH, reflux). See: (a) Ito, Y.; Sawamura, M.; Hayahsi, T. Tetrahedron Lett. 1988, 29, 239.
    • (1988) Tetrahedron Lett. , vol.29 , pp. 239
    • Ito, Y.1    Sawamura, M.2    Hayahsi, T.3
  • 15
    • 0342541983 scopus 로고    scopus 로고
    • (a) Chloramphenicol has been assigned as a generic name to the compound D-(-)-threo-N-(1,1′-dihydroxy-1-p-nitrophenylisopropyl)-dichloroacetamide for which Parke, Davis and Co. has adopted 'Chloromycetin' as its trademark
    • (a) Chloramphenicol has been assigned as a generic name to the compound D-(-)-threo-N-(1,1′-dihydroxy-1-p-nitrophenylisopropyl)-dichloroacetamide for which Parke, Davis and Co. has adopted 'Chloromycetin' as its trademark.
  • 19
    • 0030976217 scopus 로고    scopus 로고
    • (c)
    • (c) Hazra, B. G. et al. Syn. Comm. 1997, 27(11), 1857.
    • (1997) Syn. Comm. , vol.27 , Issue.11 , pp. 1857
    • Hazra, B.G.1
  • 20
    • 0343847599 scopus 로고    scopus 로고
    • (a) The absolute configuration was assumed from the results in Ref. 4 and confirmed later by comparison of the optical rotation with that reported for chloramphenicol (2)
    • (a) The absolute configuration was assumed from the results in Ref. 4 and confirmed later by comparison of the optical rotation with that reported for chloramphenicol (2).
  • 21
    • 0342976309 scopus 로고    scopus 로고
    • (b) The enantiomeric purity (ee) was determined by HPLC analysis using a Daicel Chiralcel OJ column
    • (b) The enantiomeric purity (ee) was determined by HPLC analysis using a Daicel Chiralcel OJ column.
  • 22
    • 0342976307 scopus 로고    scopus 로고
    • 3 solution
    • 3 solution.
  • 23
    • 0343847598 scopus 로고    scopus 로고
    • Keeping the reaction mixture at 40°C was crucial for good yields of the azide 6.
    • Keeping the reaction mixture at 40°C was crucial for good yields of the azide 6.
  • 35
    • 0342541979 scopus 로고    scopus 로고
    • 3 solution. The enantiomeric purity (ee) was determined later from its derivative because 10 is readily converted into the corresponding α,β-epoxy ester under basic conditions. The absolute configuration was assumed from the results in Ref. 4 and confirmed later by comparison of the optical rotation with that reported for the final product, acetyl (D)-threo-sphingosine
    • 3 solution. The enantiomeric purity (ee) was determined later from its derivative because 10 is readily converted into the corresponding α,β-epoxy ester under basic conditions. The absolute configuration was assumed from the results in Ref. 4 and confirmed later by comparison of the optical rotation with that reported for the final product, acetyl (D)-threo-sphingosine.
  • 36
    • 0342541980 scopus 로고    scopus 로고
    • 1H NMR analysis at 500 MHz. There was no detectable amount of the other enantiomer
    • 1H NMR analysis at 500 MHz. There was no detectable amount of the other enantiomer.
  • 38
    • 0342976304 scopus 로고    scopus 로고
    • This research was assisted financially by a grant from the National Institutes of Health
    • This research was assisted financially by a grant from the National Institutes of Health.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.