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Volumn 56, Issue 5, 2000, Pages 781-790

A chemoenzymatic access to D- and L-sphingosines employing hydroxynitrile lyases

Author keywords

Hydroxynitrile lyases; Selective coupling; Sphingosines

Indexed keywords

HYDROXYNITRILE LYASE; LYASE; SPHINGOSINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034723252     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)01024-8     Document Type: Article
Times cited : (42)

References (59)
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    • (b) Effenberger, F.; Ziegler, T.; Förster, S. Angew. Chem. 1987, 99, 491; Angew. Chem. Int. Ed. Engl. 1987, 26, 458.
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    • note
    • 16 system.
  • 33
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    • note
    • Variation of the amount of hydrogen cyanide used in the reaction (1-6 equiv.) or of the temperature at which the cyanide addition was performed (-78°C to RT) showed no positive improvement on the resultant diastereoselectivity of the amine 3.
  • 36
    • 85038066986 scopus 로고    scopus 로고
    • note
    • A 3:1 diastereomeric mixture of diols 10 was obtained. This mixture was inseparable by column chromatography and the stereochemical preference for this reaction was not determined.
  • 37
    • 85038052880 scopus 로고    scopus 로고
    • note
    • 2) ozonolysis was performed a slightly lower yield for the formation of the aldehyde was obtained (82%).
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    • (a) Schlosser, M.; Christmann, K. F. Angew. Chem. 1966, 78, 115; Angew. Chem. Int. Ed. Engl. 1966, 5, 126.
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    • note
    • 2 is crucial. The best quality was that purchased from Johnson Matthey GmbH, (Karlsruhe, Germany) which was pale gray in appearance. The same reagent purchased from Sigma-Aldrich or Fluka was found to be green in appearance and gave lower yields.
  • 52
    • 85038063098 scopus 로고    scopus 로고
    • note
    • a a R=H 5 10 b R=TBDMS 15 30 c R=TIPS 10 76 c R=TIPS 5 91.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.