Salinomycin → 20-Deoxysalinomycin

HRID 1742154Notes

Reaction equation

HRID 1742154 reaction equation
[CH3:1][CH2:2][C@@H:3]([C:51]([OH:53])=[O:52])[C@@H:4]1[O:9][C@@H:8]([C@H:10]([C@H:12]([OH:49])[C@@H:13]([C:15]([C@@H:17]([C@H:20]2[O:25][C@@:24]3([O:30][C@:29]4([O:34][C@@:33]([C@@H:36]5[O:41][C@@H:40]([CH3:42])[C@@:39]([OH:45])([CH2:43][CH3:44])[CH2:38][CH2:37]5)([CH3:35])[CH2:32][CH2:31]4)[C@H:28]([OH:46])[CH:27]=[CH:26]3)[C@H:23]([CH3:47])[CH2:22][C@@H:21]2[CH3:48])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[C@@H:7]([CH3:50])[CH2:6][CH2:5]1>C(OCC)(=O)C>[CH3:1][CH2:2][C@@H:3]([C:51]([OH:53])=[O:52])[C@@H:4]1[O:9][C@@H:8]([C@H:10]([C@H:12]([OH:49])[C@@H:13]([C:15]([C@@H:17]([C@H:20]2[O:25][C@@:24]3([O:30][C@:29]4([O:34][C@@:33]([C@@H:36]5[O:41][C@@H:40]([CH3:42])[C@@:39]([OH:45])([CH2:43][CH3:44])[CH2:38][CH2:37]5)([CH3:35])[CH2:32][CH2:31]4)[C@H:28]([OH:46])[CH:27]=[CH:26]3)[C@H:23]([CH3:47])[CH2:22][C@@H:21]2[CH3:48])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[C@@H:7]([CH3:50])[CH2:6][CH2:5]1.[CH3:1][CH2:2][CH:3]([C:51]([OH:53])=[O:52])[CH:4]1[O:9][CH:8]([CH:10]([CH:12]([OH:49])[CH:13]([C:15]([CH:17]([CH:20]2[O:25][C:24]3([O:30][C:29]4([O:34][C:33]([CH:36]5[O:41][CH:40]([CH3:42])[C:39]([OH:45])([CH2:43][CH3:44])[CH2:38][CH2:37]5)([CH3:35])[CH2:32][CH2:31]4)[CH2:28][CH:27]=[CH:26]3)[CH:23]([CH3:47])[CH2:22][CH:21]2[CH3:48])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[CH:7]([CH3:50])[CH2:6][CH2:5]1

Participants

4

Reactant 1

HCID 3085092Salinomycin

Product 2

HCID 19846420-DeoxysalinomycinHCID 3085092Salinomycin

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Fifty grams of the crude salinomycin powder is dissolved in ethyl acetate and applied to column (50 g of active almina, commercial product of Wako Junyaku Co.). After washing the column with one liter of ethyl acetate, salinomycin and SY-1 are eluted with a 100:5 mixture of ethyl acetate-methanol solution. The fractions containing salinomycin and SY-1 are combined and concentrated. The concentrate is diluted in 50 ml of chloroform-methand solution (100:2) and applied to the column of 300 g silica gel (Wakogel-200, Wako Junyaku Co.) packed in the same solvent mixture. Elution is carried out with the same solvent mixture to give pure salinomycin fraction and pure SY-1 fraction. Each fraction is concentrated and crystallized from acetone-water solution to give 5 g of salinomycin and 30 mg of SY-1 in pure crystals, respectively.

Workup

  1. washAfter washing the column with one liter of ethyl acetate, salinomycin and SY-1
  2. washare eluted with a 100:5 mixture of ethyl acetate-methanol solution
  3. additionThe fractions containing salinomycin and SY-1
  4. concentrationconcentrated
  5. additionThe concentrate is diluted in 50 ml of chloroform-methand solution (100:2)
  6. washElution

Sources & evidence

ORD record
ord-97040f87288b4270ae5afddbc4b740a3
Source dataset
uspto-grants-1994_08
Patent number
USRE034698

Reaction notes

Loading…