Sodium Hydroxide → 5-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranoside

HRID 1247747Notes

Reaction equation

HRID 1247747 reaction equation
C([O:4][C@@H:5]1[C@@H:32]([O:33]C(=O)C)[C@H:31]([O:37]C(=O)C)[C@@H:30]([CH2:41][O:42]C(=O)C)[O:29][C@H:6]1[O:7][C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)(=O)C.[OH-].[Na+]>CO>[O:7]([C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][O:25][CH2:26][O:27][CH3:28])=[CH:19][CH:18]=1)[C@@H:6]1[O:29][C@H:30]([CH2:41][OH:42])[C@@H:31]([OH:37])[C@H:32]([OH:33])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 12085609HCID 12085609, compound

Product 1

HCID 688708525-methoxy-2-(4-[2-(methoxymethyloxy)ethyl]benzyl)phenyl beta-D-glucopyranosideYield 55.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-methoxy-2-{4-[2-(methoxymethyl-oxy)ethyl]benzyl}phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.13 g) in methanol (8 mL) was added 2 mol/L aqueous sodium hydroxide solution (0.50 mL), and the mixture was stirred at room temperature for 25 minutes. The solvent was removed under reduced pressure, and the residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=7/1) to give 5-methoxy-2-{4-[2-(methoxymethyloxy)ethyl]benzyl}phenyl β-D-glucopyranoside (0.053 g).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=7/1)

Sources & evidence

ORD record
ord-4693cbbe6ae64fe9b95d6203438c4edc
Source dataset
uspto-grants-2006_10
Patent number
US07129381B2

Reaction notes

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