Methanol → Deacetylasperulosidic acid methyl ester

HRID 1089628Notes

Reaction equation

HRID 1089628 reaction equation
CC([O:4][CH2:5][C:6]1[C@H:10]2[C@H:11]([O:18][C@@H:19]3[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]([OH:28])[C@H:20]3[OH:29])[O:12][CH:13]=[C:14]3[C:15]([O:17][C@H:8]([C@@H:9]23)[CH:7]=1)=[O:16])=O.[CH3:30][OH:31]>O>[CH3:30][O:31][C:15]([C:14]1[C@H:9]2[C@@H:8]([OH:17])[CH:7]=[C:6]([CH2:5][OH:4])[C@H:10]2[C@H:11]([O:18][C@@H:19]2[O:24][C@H:23]([CH2:25][OH:26])[C@@H:22]([OH:27])[C@H:21]([OH:28])[C@H:20]2[OH:29])[O:12][CH:13]=1)=[O:16]

Participants

4

Reactant 2

HCID 887MethanolHCID 84298ASPERULOSIDE

Product 1

HCID 6325021Deacetylasperulosidic acid methyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Asperuloside (1.0 g) was dissolved in distilled water (10 ml) and adjusted to pH=10 by adding a small amount of a saturated solution of BaO in methanol. This solution was allowed to stand for a few minutes to become cloudy white, which, after neutralization and concentration, was treated by silica gel column chromatography (Waco Gel C-300, 50 g, solvent: chloroform-methanol system). Silica gel column chromatography gave deacetyl asperulosidic acid methyl ester having Rf value=0.79 (chloroform-methanol-water=6:6:1, visualized with 50(%)-sulfuric acid) on TLC, as white needles (1.80 mg).

Workup

  1. waitto stand for a few minutes
  2. concentrationwhich, after neutralization and concentration
  3. additionwas treated by silica gel column chromatography (Waco Gel C-300, 50 g, solvent: chloroform-methanol system)

Sources & evidence

ORD record
ord-5ee8e7015ab34d36a1781d653442ed80
Source dataset
uspto-grants-1992_01
Patent number
US05078750

Reaction notes

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