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Volumn 4, Issue 10, 2002, Pages 1719-1722

Synthesis of D-erythro-dihydrosphingosine and D-xylo-phytosphingosine from a serine-derived 1,5-dioxaspiro[3.2]hexane template

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIOXASPIRO(3.2)HEXANE; 1,5-DIOXASPIRO(3.2)HEXANE; DRUG DERIVATIVE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; ERYTHRO-DIHYDROSPHINGOSINE; HETEROCYCLIC COMPOUND; IMMUNOSUPPRESSIVE AGENT; SERINE; SPHINGANINE; SPHINGOSINE; SPIRO COMPOUND; XYLO PHYTOSPHINGOSINE; XYLO-PHYTOSPHINGOSINE;

EID: 0037118355     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0200448     Document Type: Article
Times cited : (59)

References (29)
  • 10
    • 0031873509 scopus 로고    scopus 로고
    • Approaches to sphingosines (Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. Curfman, D.; Liotta, D. Methods Enzymol. 2000, 311, 391-440) and phytosphingosines (Howell, A. R.; Ndakala, A. J. Curr. Org. Chem., in press) have been recently reviewed.
    • (1998) Synthesis , pp. 1075-1091
    • Koskinen, P.M.1    Koskinen, A.M.P.2
  • 11
    • 0032717309 scopus 로고    scopus 로고
    • and phytosphingosines
    • Approaches to sphingosines (Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. Curfman, D.; Liotta, D. Methods Enzymol. 2000, 311, 391-440) and phytosphingosines (Howell, A. R.; Ndakala, A. J. Curr. Org. Chem., in press) have been recently reviewed.
    • (2000) Methods Enzymol. , vol.311 , pp. 391-440
    • Curfman, D.1    Liotta, D.2
  • 12
    • 0042541495 scopus 로고    scopus 로고
    • in press have been recently reviewed
    • Approaches to sphingosines (Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091. Curfman, D.; Liotta, D. Methods Enzymol. 2000, 311, 391-440) and phytosphingosines (Howell, A. R.; Ndakala, A. J. Curr. Org. Chem., in press) have been recently reviewed.
    • J. Curr. Org. Chem.
    • Howell, A.R.1    Ndakala, A.2
  • 20
    • 0042040647 scopus 로고    scopus 로고
    • note
    • Compound 1 was isolated as a mixture of diastereomers (95/5). The identity of the major diastereomer is not known. Evidence (see ref 9) suggests that diastereoselectivity is largely sterically controlled. It is noteworthy that the diastereomeric ratio is inconsequential for the subsequent transformations of 1 in the applications described in this Letter.
  • 29
    • 0001332620 scopus 로고
    • Eliel and Frye and co-workers have shown (see: Chen, X.; Hortelano, E. R.; Eliel, E. L.; Frye, S. V. J. Am. Chem. Soc. 1992, 114, 1778-1784) that the addition of Grignard reagents to α-siloxy ketones proceeds via chelated transition states to varying degrees. However, there is evidence that TES ethers can participate in chelatation to a significant extent. Due to competing steric effects of the bulky BOC-protected oxazolidine and the TES ether, it would be anticipated that an open transition state would afford low levels of diastereoselectivity. The lower diastereoselectivity at -10°C in comparison to that at -78°C can be attributed to the reaction proceeding through a mixture of chelated and open transition states with reaction through the chelated intermediate predominating to a greater extent at the lower temperature.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 1778-1784
    • Chen, X.1    Hortelano, E.R.2    Eliel, E.L.3    Frye, S.V.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.