Phyllanthostatin 1 → NSC345395

反応式

[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

参加物

反応物 2

HCID 5358585Phyllanthostatin 1

HCID 6436218phyllanthoside2 回

生成物 2

HCID 5477680NSC345395

HCID 6436218phyllanthoside

実験手順

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.

出典と根拠

ORDレコード: ord-2347662e24a148cab478ca51e4672cbe
出典データセット: uspto-grants-1983_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US04388457

反応ノート

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