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Volumn 54, Issue 36, 1998, Pages 10657-10670

A short and efficient synthesis of phytosphingosines using asymmetric dihydroxylation

Author keywords

[No Author keywords available]

Indexed keywords

PHYTOSPHINGOSINE; PROTEIN KINASE C INHIBITOR; SPHINGOLIPID; SPHINGOSINE 1 PHOSPHATE; UNCLASSIFIED DRUG;

EID: 0032480389     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00615-2     Document Type: Article
Times cited : (61)

References (40)
  • 29
    • 85038536449 scopus 로고    scopus 로고
    • note
    • 1H NMR data are shown in experimental section. (formula presented)
  • 33
    • 85038533344 scopus 로고    scopus 로고
    • note
    • 9. The dihydroxylation using the bulky DHQ or DHQD ligated osmium reagent was very sluggish. Most of (Z)-3 was almost recovered along with a small amount of phenyl ketone compounds, which would be oxydized products of diols 9 and 10.
  • 37
    • 11944249437 scopus 로고
    • 4 and the allylic substituent, in which the acidity of the latter was a crucial factor. Accordingly, the acidic NH proton of the allylic NHBoc group of (Z)-5 and (Z)-6 might affect the selectivity so as to make syn attack of the reagent prefered. b) Cha, J. K.; Kim, N.-S. Chem. Rev. 1995, 95, 1761.
    • (1995) Chem. Rev. , vol.95 , pp. 1761
    • Cha, J.K.1    Kim, N.-S.2
  • 38
    • 0028210293 scopus 로고
    • 12. In general, it is known to be difficult to achieve stereoselective dihydroxylation of (Z)-olefins using AD-mix reagents. The high selectivities attained here might be explained by the effect of hydrogen bonding between homoallyl alcohol moiety of the deprotected (Z)-olefins and oxo group on osmium as suggested by Sharpless: see, VanNieuwenhze, M. S.; Sharpless, K. B. Tetrahedron Lett. 1994, 35, 843.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 843
    • VanNieuwenhze, M.S.1    Sharpless, K.B.2
  • 39
    • 85038534121 scopus 로고    scopus 로고
    • note
    • 13. The X-ray crystallographic data of the compound 13c have been deposited to Cambridge Crystallographic Data Center.
  • 40
    • 85038531201 scopus 로고    scopus 로고
    • note
    • 5h of the optical rotation of the compound 17 has ever been made, but the reason for the large difference between the value of the optical rotation obtained by us and the reference's one is not clear.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.