Sodium Methoxide → Ethyl D-glucoside

HRID 1612915Notes

Reaction equation

HRID 1612915 reaction equation
C([O:4][C@@H:5]1[C@@H:13]([O:14]C(=O)C)[C@H:12]([O:18]C(=O)C)[C@@H:11]([CH2:22][O:23]C(=O)C)[O:10][CH:6]1[O:7][CH2:8][CH3:9])(=O)C.C[O-].[Na+]>CO>[O:7]([CH2:8][CH3:9])[C@@H:6]1[O:10][C@H:11]([CH2:22][OH:23])[C@@H:12]([OH:18])[C@H:13]([OH:14])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54493907HCID 54493907, compound

Product 1

HCID 121667Ethyl D-glucoside

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The ethyl 2,3,4,6-tetra-O-acetyl-glucopyranoside was deacetylated with 1M sodium methoxide (2 ml) in Methanol (80 ml) for 20 hours at room temperature. The mixture was neutralized with Amberlite™ IR-120 (H+ -form) and concentrated in vacuo to give the product in quantitative yield as a hygroscopic solid.

Workup

  1. concentrationconcentrated in vacuo
  2. customto give the product in quantitative yield as a hygroscopic solid

Sources & evidence

ORD record
ord-7281024790d34009b59d906802dbfe5f
Source dataset
uspto-grants-1993_03
Patent number
US05191071

Reaction notes

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