20-Deoxysalinomycin → HCID 131711806, compound

HRID 2057789Notes

Reaction equation

HRID 2057789 reaction equation
[CH3:1][CH2:2][CH:3]([C:50]([OH:52])=[O:51])[CH:4]1[O:9][CH:8]([CH:10]([CH:12]([OH:48])[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]([CH3:46])[CH2:22][CH:21]2[CH3:47])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[CH:7]([CH3:49])[CH2:6][CH2:5]1.C(OCC)(=[O:55])C.CO>CCCCCC.C(OCC)(=O)C>[CH3:1][CH2:2][C@@H:3]([C:50]([OH:52])=[O:51])[C@@H:4]1[O:9][C@@H:8]([C@H:10]([C@H:12]([OH:48])[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:55])[CH:27]=[CH:26]3)[C@H:23]([CH3:46])[CH2:22][C@@H:21]2[CH3:47])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[C@@H:7]([CH3:49])[CH2:6][CH2:5]1.[CH3:1][CH2:2][CH:3]([C:50]([OH:52])=[O:51])[CH:4]1[O:9][CH:8]([CH:10]([CH:12]([OH:48])[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]([CH3:46])[CH2:22][CH:21]2[CH3:47])[CH2:18][CH3:19])=[O:16])[CH3:14])[CH3:11])[CH:7]([CH3:49])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 19846420-DeoxysalinomycinHCID 21584119Ethylacetate methanol

Product 1

HCID 131711806HCID 131711806, compound

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

The mother liquor separated from crystals in the process in (D) is concentrated to dryness to give 9.7 kg of the complex containing SY-1 through -8. The complex is dissolved in 100 liters of a 2:1 mixture of hexane-ethyl acetate, applied to the column of 20 kg of almina in the same manner as described in Example 2 (E) and developed with 30 liters of a 100:2 mixture of ethyl acetate-methanol to elute SY-1, SY-3 and SY-7. The effluent is treated in the same manner as described in Example 2 (E) to give 400 g of salinomycin-SY-1 mixture and 130 g of crude powder containing SY-3 and SY-7.

Workup

  1. washto elute SY-1
  2. additionThe effluent is treated in the same manner

Sources & evidence

ORD record
ord-b5e5d96ac8d74d5c8fc7426f6ffc6b5f
Source dataset
uspto-grants-1980_07
Patent number
US04212942

Reaction notes

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