Phyllanthostatin 1 → NSC345395

HRID 2166743Notes

Reaction equation

[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

Participants

Reactant 2

HCID 5358585Phyllanthostatin 1

HCID 643621863166-73-42×

Product 2

HCID 5477680NSC345395

HCID 643621863166-73-4

Procedure

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.

Sources & evidence

ORD record: ord-2347662e24a148cab478ca51e4672cbe
Source dataset: uspto-grants-1983_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04388457

Reaction notes

Loading…