Phyllanthostatin 1 → NSC345395

HRID 2166743Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2166743
[CH3:1][C@@H:2]1[C@H:7]([O:8][C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6][C:5]2([O:28][C@@H:27]3[C@@H:22]([CH2:23][CH2:24][C@@H:25]([C:29]([O:31][CH:32]4OC(C)C(OC5OC(C)C(O)C(OC(C)=O)C5O)C(OC(C)=O)C4O)=[O:30])[CH2:26]3)[C@:19]32[O:21][CH2:20]3)[O:4][CH2:3]1.[CH3:58][C@H:59]1[C@@H:64]([O:65][C:66](/[CH:68]=[CH:69]/[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)=[O:67])[CH2:63][C@@:62]2([O:85][C@@H:84]3[C@@H:79]([CH2:80][CH2:81][C@H:82]([C:86]([O:88][C@@H:89]4[O:94][C@H:93]([CH3:95])[C@@H:92]([OH:96])[C@H:91]([O:97][C:98]([CH3:100])=[O:99])[C@H:90]4[O:101][C@@H:102]4[O:107][C@H:106]([CH3:108])[C@@H:105]([OH:109])[C@H:104]([O:110][C:111]([CH3:113])=[O:112])[C@H:103]4[OH:114])=[O:87])[CH2:83]3)[C@@:76]32[O:78][CH2:77]3)[O:61][CH2:60]1>>[CH3:58][C@H:59]1[C@@H:64]([O:65][C:66](/[CH:68]=[CH:69]/[C:70]2[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=2)=[O:67])[CH2:63][C@@:62]2([O:85][C@@H:84]3[C@@H:79]([CH2:80][CH2:81][C@H:82]([C:86]([O:88][C@@H:89]4[O:94][C@H:93]([CH3:95])[C@@H:92]([OH:96])[C@H:91]([O:97][C:98]([CH3:100])=[O:99])[C@H:90]4[O:101][C@@H:102]4[O:107][C@H:106]([CH3:108])[C@@H:105]([OH:109])[C@H:104]([O:110][C:111]([CH3:113])=[O:112])[C@H:103]4[OH:114])=[O:87])[CH2:83]3)[C@@:76]32[O:78][CH2:77]3)[O:61][CH2:60]1.[CH3:1][CH:2]1[CH:7]([O:8][C:9](/[CH:11]=[CH:12]/[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:6][C:5]2([O:28][CH:27]3[CH:22]([CH2:23][CH2:24][CH:25]([C:29]([O:31][CH3:32])=[O:30])[CH2:26]3)[C:19]32[O:21][CH2:20]3)[O:4][CH2:3]1

Komponenten

4

Edukt 2

HCID 5358585Phyllanthostatin 1HCID 6436218phyllanthoside2×

Produkt 2

HCID 5477680NSC345395HCID 6436218phyllanthoside

Versuchsvorschrift

The complete structures of phyllanthostatin 1 and phyllanthoside were deduced by interpreting the 13C NMR (22.63 MHz, CDCl3), 1H NMR (400 MHz, CDCl3) and EI high resolution and FD mass spectra. Although the structure of phyllanthoside was not previously known, Kupchan and co-workers reported [Kupchan, S. M., supra] structural studies of two degradation products which proved very useful in the present study. Methanolysis of phyllanthoside gave an aglycone methyl ester, phyllanthocin (determined by X-ray crystallographic analysis) and a disaccharide, C12H22O9. Acid hydrolysis of the disaccharide yielded 6-deoxy-D-glucose and spectral evidence suggested that the disaccharide portion contained two acetate groups.

Quellen und Nachweise

ORD-Eintrag
ord-2347662e24a148cab478ca51e4672cbe
Quelldatensatz
uspto-grants-1983_06
Patentnummer
US04388457

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