Sodium Methoxide → phenyl thio-beta-D-galactopyranoside

HRID 1510173Notes

Reaction equation

HRID 1510173 reaction equation
C([O:4][C@@H:5]1[C@@H:17]([O:18]C(=O)C)[C@@H:16]([O:22]C(=O)C)[C@@H:15]([CH2:26][O:27]C(=O)C)[O:14][C@H:6]1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.C[O-].[Na+]>CO>[S:7]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C@@H:6]1[O:14][C@H:15]([CH2:26][OH:27])[C@H:16]([OH:22])[C@H:17]([OH:18])[C@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 10950254Phenyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-galactopyranoside

Product 1

HCID 2802071phenyl thio-beta-D-galactopyranoside

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 8 (31.7 g, 72.07 mmol, 1 eq) dissolved in dry MeOH (800 mL) under argon was added sodium methanolate (17.3 g, 302.7 mmol, 4.2 eq). After being stirred for 1 h, Amberlite IR 120 (300 g) was added and the mixture was stirred for 15 min up to pH=7. The solution was filtered through alumina. The cake was washed with MeOH (150 mL) and the organic layer was concentrated. The crude was engaged in the next step.

Workup

  1. stirringthe mixture was stirred for 15 min up to pH=7
  2. filtrationThe solution was filtered through alumina
  3. washThe cake was washed with MeOH (150 mL)
  4. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-dc838f6803ac48cebf7b58de758447a4
Source dataset
uspto-grants-2012_07
Patent number
US08211859B2

Reaction notes

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