Anemoside A3 → HCID 21672692, compound

HRID 237244Notes

Reaction equation

CO.Cl.C[C@@H]1O[C@@H](O[C@H]2[C@H]([O:18][C@@H:19]3[C@:39]([CH2:41][OH:42])([CH3:40])[C@H:38]4[C@@:22]([CH3:51])([C@@H:23]5[C@@:35]([CH3:43])([CH2:36][CH2:37]4)[C@@:34]4([CH3:44])[C@@H:26]([C@@H:27]6[C@@:31]([C:45]([OH:47])=[O:46])([CH2:32][CH2:33]4)[CH2:30][CH2:29][C@H:28]6[C:48]([CH3:50])=[CH2:49])[CH2:25][CH2:24]5)[CH2:21][CH2:20]3)OC[C@H](O)[C@@H]2O)[C@H](O)[C@H](O)[C@H]1O>O>[CH3:50][C:48]([C@H:28]1[C@@H:27]2[C@@H:26]3[C@@:34]([CH3:44])([CH2:33][CH2:32][C@@:31]2([C:45]([OH:47])=[O:46])[CH2:30][CH2:29]1)[C@@:35]1([CH3:43])[C@@H:23]([C@:22]2([CH3:51])[C@@H:38]([CH2:37][CH2:36]1)[C@@:39]([CH2:41][OH:42])([CH3:40])[C@@H:19]([OH:18])[CH2:20][CH2:21]2)[CH2:24][CH2:25]3)=[CH2:49]

Participants

Conditions

Temperature: 35 °C

Procedure

To a solution of HCl methanol reagent 10 (10 mL) was added Pulchinenoside A (DA001, 100 mg) and the resulting mixture was stirred at 35° C. for 4 days. After pouring into water (10 ml), the mixture was extracted with chloroform (3×50 ml). The combined organic layer was washed with H2O (1×10 ml), brine (1×10 ml), dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel using CH2Cl2-MeOH (v/v, 30:1) to yield the desired product as a white solid with 85% yield.

Workup

extractionthe mixture was extracted with chloroform (3×50 ml)
washThe combined organic layer was washed with H2O (1×10 ml), brine (1×10 ml)
dry with materialdried over sodium sulfate
concentrationconcentrated under vacuum
customThe resulting residue was purified by column chromatography on silica gel

Sources & evidence

ORD record: ord-312fed1d8a574dd7bf5e643e5a198099
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642567B2

Reaction notes

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