Digitoxin → Deslanoside

HRID 2391034Notes

Reaction equation

C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3C(=O)C4C(O)=CC(O)=CC=4OC=3C3C=CC(O)=C(O)C=3)[C@H](O)[C@@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O.C[C@H]1O[C@@H](O[C@H]2[C@@H](O)C[C@H](O[C@H]3[C@@H](O)C[C@H](O[C@@H]4C[C@H]5CC[C@H]6[C@@]7(O)CC[C@H](C8COC(=O)C=8)[C@@]7(C)CC[C@@H]6[C@@]5(C)CC4)O[C@@H]3C)O[C@@H]2C)C[C@H](O)[C@@H]1O.[CH3:98][C@H:99]1[O:104][C@@H:103]([O:105][C@@H:106]2[CH2:111][C@H:110]3[CH2:112][CH2:113][C@H:114]4[C@@:119]5([OH:129])[CH2:120][CH2:121][C@H:122]([C:123]6[CH2:128][O:127][C:125](=[O:126])[CH:124]=6)[C@@:118]5([CH3:130])[C@H:117]([OH:131])[CH2:116][C@@H:115]4[C@@:109]3([CH3:132])[CH2:108][CH2:107]2)[CH2:102][C@H:101]([OH:133])[C@@H:100]1[O:134][C@@H:135]1[O:140][C@H:139]([CH3:141])[C@@H:138]([O:142][C@@H:143]2[O:148][C@H:147]([CH3:149])[C@@H:146]([O:150][C@@H:151]3[O:156][C@H:155]([CH2:157][OH:158])[C@@H:154]([OH:159])[C@H:153]([OH:160])[C@H:152]3[OH:161])[C@@H:145]([O:162]C(C)=O)[CH2:144]2)[C@@H:137]([OH:166])[CH2:136]1>>[CH3:98][C@H:99]1[O:104][C@@H:103]([O:105][C@@H:106]2[CH2:111][C@H:110]3[CH2:112][CH2:113][C@H:114]4[C@@:119]5([OH:129])[CH2:120][CH2:121][C@H:122]([C:123]6[CH2:128][O:127][C:125](=[O:126])[CH:124]=6)[C@@:118]5([CH3:130])[C@H:117]([OH:131])[CH2:116][C@@H:115]4[C@@:109]3([CH3:132])[CH2:108][CH2:107]2)[CH2:102][C@H:101]([OH:133])[C@@H:100]1[O:134][C@@H:135]1[O:140][C@H:139]([CH3:141])[C@@H:138]([O:142][C@@H:143]2[O:148][C@H:147]([CH3:149])[C@@H:146]([O:150][C@@H:151]3[O:156][C@H:155]([CH2:157][OH:158])[C@@H:154]([OH:159])[C@H:153]([OH:160])[C@H:152]3[OH:161])[C@@H:145]([OH:162])[CH2:144]2)[C@@H:137]([OH:166])[CH2:136]1

Participants

Reactant 3

HCID 441207Digitoxin

HCID 656630Lanatoside C2×

HCID 5280805Rutin

Product 1

HCID 28620Deslanoside

Procedure

Further, rutin is a flavonoid glycoside which is contained in buckwheat and tea leaves. Digitoxin is colorless white-crystalline powder which is contained in digitalis. Lanatoside C is much contained in digitalis lanata. Lanatoside C is hydrolyzed with alkali to obtain deslanoside. Deslanoside is removed of glucose by an enzyme reaction to obtain digoxin. Strophanthin is a glycoside contained in apocynaceae plants. Glycyrrhizin and glycyrrhizard are colorless crystal contained in licorice roots. Amygdalin is much contained in bitter almond and fruit nucleus. Arbutin exists in rhododendron plants, and plants such as cowberry and uva-ursi.

Workup

customleaves

Sources & evidence

ORD record: ord-04c2854045a0444c84305c22f070f744
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273906B2

Reaction notes

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