Sodium Methoxide → HCID 68872440, compound

HRID 1982825Notes

Reaction equation

HRID 1982825 reaction equation
C[O-].[Na+].C([O:7][C@@H:8]1[C@@H:31]([O:32]C(=O)C)[C@H:30]([O:36]C(=O)C)[C@@H:29]([CH2:40][O:41]C(=O)C)[O:28][C@H:9]1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH:26]=[CH2:27])=[CH:20][CH:19]=1)(=O)C>CO.O1CCCC1>[O:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH:26]=[CH2:27])=[CH:22][CH:23]=1)[C@@H:9]1[O:28][C@H:29]([CH2:40][OH:41])[C@@H:30]([OH:36])[C@H:31]([OH:32])[C@H:8]1[OH:7]

Participants

5

Reactant 2

HCID 10942334Sodium MethoxideHCID 12085580HCID 12085580, compound

Product 1

HCID 68872440HCID 68872440, compoundYield 74.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium methoxide (28% methanol solution; 0.030 mL) was added to a solution of 2-(4-allyloxybenzyl)phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (0.44 g) in methanol (2.5 mL) and tetrahydrofuran (1.5 mL), and the mixture was stirred at room temperature for 4 hours. The solvent of the reaction mixture was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 2-(4-allyloxybenzyl)phenyl β-D-glucopyranoside (0.23 g).

Workup

  1. customThe solvent of the reaction mixture was removed under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-33ebbd5848144464845f30e6e366671f
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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