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  • 1
    ISSN: 0170-2041
    Keywords: Hormones of plants ; Gibberellins, labelled ; Glucosyl conjugates ; Koenigs-Knorr reaction ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2-O-GA29β-D-glucopyranoside (1e) and 13-O-GA29, β-D-glucopyr-anoside (1h) were synthesized from GA29 methyl ester (1b). Their structures were confirmed by 1H NMR and GC-MS. Likewise, [17-13C,T2]-labelled 1e and 1h could be obtained. From [17-13C,T2]GA20 (2a) and [17-13C,T2]GA5 (3a) the 13-O-GA β-D-[6-D2]glucopyranosides [17-13C,T2;6′-D2]-2d and [17-13C,T2;6′-D2]-3d, and the β-D-glucopyranosyl esters [17-13C,T2;6′-D2]-2f and [17-13C,T2;6′-D2]-3f were synthesized. The labelled compounds were characterized by HPLC and GC-MS.
    Additional Material: 3 Tab.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 519-524 
    ISSN: 0170-2041
    Keywords: Soladunalinidine ; 5α-Tomatidan-3β-amine ; 5α-Solasodan-3α-amine and -3β-amine ; 5α-Spirosolan-3-amines ; Solanum steroid alkaloids ; Steroids ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The steroid alkaloid soladunalinidine [5α-tomatidan-3β-amine, (25S)-5α,22βN-spirosolan-3β-amine, 2], isolated from Solanum dunalianum, is synthesized from tomatidine (5α-tomatidan-3β-ol, 1) via 5α-tomatidan-3-one (4) and its oxime 5 which is reduced to 2 as well as to its ring-E-opened (22S) and (22R) dihydro products 6 and 9, the N(22,26)-chloro-N(3)-(2-hydroxy-benzylidene) derivatives 8 and 11 of which are recyclized to N(3)-(2-hydroxybenzylidene)soladunalinidine (3). The 5α-spirosolan-3-amines stereoisomeric at C-22 and C-25, 5α-solasodan-3α-amine (13) and -3β-amine (15), are obtained in an analogous sequence of reactions from soladulcidine (5α-solasodan-3β-ol, 12).
    Type of Medium: Electronic Resource
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