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Volumn 75, Issue 15, 2010, Pages 5363-5366

Synthesis of the sulfonate analogue of seminolipid via horner-wadsworth- emmons olefination

Author keywords

[No Author keywords available]

Indexed keywords

DOUBLE BONDS; STEREO-SELECTIVE; WADSWORTH-EMMONS OLEFINATION;

EID: 77955161524     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1008788     Document Type: Article
Times cited : (15)

References (38)
  • 2
    • 68749095950 scopus 로고    scopus 로고
    • For evidence that in mouse testis, besides the major molecule 1a, some (C16:0-alkyl-C14:0-acyl), (C14:0-alkyl-C16:0-acyl), and (C17:0-alkyl-C16:0-acyl) species are expressed during testicular maturation, see
    • For evidence that in mouse testis, besides the major molecule 1a, some (C16:0-alkyl-C14:0-acyl), (C14:0-alkyl-C16:0-acyl), and (C17:0-alkyl-C16:0-acyl) species are expressed during testicular maturation, see: Goto-Inoue, N.; Hayasaka, T.; Zaima, N.; Setou, M. Glycobiology 2009, 19, 950-957
    • (2009) Glycobiology , vol.19 , pp. 950-957
    • Goto-Inoue, N.1    Hayasaka, T.2    Zaima, N.3    Setou, M.4
  • 29
    • 84855623681 scopus 로고    scopus 로고
    • 1′,2′ = 8.0 Hz
    • 1′,2′ = 8.0 Hz.
  • 32
    • 84855623017 scopus 로고    scopus 로고
    • Zemplèn transesterification, performed with 1 molar eq. of sodium methoxide and stopped after 48 h, avoided TBS cleavage; in these conditions, 15% of the byproduct benzylated at position 4 and 6 but retaining the benzoate at position 2 was recovered after flash chromatography
    • Zemplèn transesterification, performed with 1 molar eq. of sodium methoxide and stopped after 48 h, avoided TBS cleavage; in these conditions, 15% of the byproduct benzylated at position 4 and 6 but retaining the benzoate at position 2 was recovered after flash chromatography.
  • 35
    • 84855617456 scopus 로고    scopus 로고
    • Preliminary attempts on tetradecanal or cyclohexanone models afforded the corresponding α,β-unsaturated sulfonates in 60-70% yield
    • Preliminary attempts on tetradecanal or cyclohexanone models afforded the corresponding α,β-unsaturated sulfonates in 60-70% yield.
  • 36
    • 77955158696 scopus 로고    scopus 로고
    • For our purposes the very difficult separation of sulfonates 2a and 2b was not required as both isomers had to stereoselectively converge to a single reduction product
    • For our purposes the very difficult separation of sulfonates 2a and 2b was not required as both isomers had to stereoselectively converge to a single reduction product.
  • 37
    • 84855637456 scopus 로고    scopus 로고
    • E/Z ratio was 2:1 according to integration of the olefinic proton (δ 6.78 ppm for E -isomer and δ 6.68 ppm for Z -isomer)
    • E/Z ratio was 2:1 according to integration of the olefinic proton (δ 6.78 ppm for E -isomer and δ 6.68 ppm for Z -isomer).
  • 38
    • 77955133089 scopus 로고    scopus 로고
    • Attempts to reduce compounds 2a,b by catalytic hydrogenation in the presence of Pt/C resulted in an incomplete reaction, and sodium borohydride showed stereoselectivity in favour of the gulo -isomer. Moreover, a difference of reactivity between 2a and 2b was observed in the hydrogenation reaction where TLC analysis showed a faster reduction of compound 2a with respect to compound 2b
    • Attempts to reduce compounds 2a,b by catalytic hydrogenation in the presence of Pt/C resulted in an incomplete reaction, and sodium borohydride showed stereoselectivity in favour of the gulo -isomer. Moreover, a difference of reactivity between 2a and 2b was observed in the hydrogenation reaction where TLC analysis showed a faster reduction of compound 2a with respect to compound 2b.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.