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Volumn 9, Issue 3, 2011, Pages 744-747

Synthesis of novel sugar-lactam conjugates using the Aubé reaction

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL DIVERSITY; CNS DRUG DELIVERY; GLYCOCONJUGATES; GLYCOMIMETICS; PEPTIDOMIMETICS; POTENTIAL APPLICATIONS;

EID: 79251497381     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c0ob00719f     Document Type: Article
Times cited : (8)

References (43)
  • 4
    • 0006077638 scopus 로고    scopus 로고
    • Synthesis of Medium-Sized Ring Lactams
    • U. Nubbemeyer Synthesis of Medium-Sized Ring Lactams Top. Curr. Chem. 2001 216 125
    • (2001) Top. Curr. Chem. , vol.216 , pp. 125
    • Nubbemeyer, U.1
  • 31
    • 79251488622 scopus 로고    scopus 로고
    • 20050153928
    • US Pat., 20050153928, 2005
    • (2005) US Pat.
  • 33
    • 0036240316 scopus 로고    scopus 로고
    • See the ESI for detailed experimental information During the alkylation step, unwanted olefin II was obtained as a major compound. The spectral data of compound 3 prepared via this route was compared with that of 3 obtained by the Aubé reaction and found to be identical. Experimental details and all other unsuccessful attempts to prepare sugar-lactam conjugate 3 are available in the ESI HPLC analysis of the reaction mixture showed a >95:5 diastereoselectivity. Only the major isomer was isolated The stereochemistry of the newly formed chiral center in compound 9 is assumed to be as drawn based on the X-ray structure of the triacetate of 8
    • X. J. Wu X. Tang M. Xian P. G. Braunschweiger P. G. Wang Bioorg. Med. Chem. 2002 10 2303
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 2303
    • Wu, X.J.1    Tang, X.2    Xian, M.3    Braunschweiger, P.G.4    Wang, P.G.5
  • 41
    • 79251473864 scopus 로고    scopus 로고
    • Along with 23 and 26, small amounts of corresponding cyclopentanone ketals VI (13%) and VII (21%) were also isolated, respectively. Their tentative structures are shown below: "chemical equation presented"
    • Along with 23 and 26, small amounts of corresponding cyclopentanone ketals VI (13%) and VII (21%) were also isolated, respectively. Their tentative structures are shown below: "chemical equation presented"


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.