Potassium Carbonate → phenyl thio-beta-D-galactopyranoside

HRID 1637428Notes

Reaction equation

HRID 1637428 reaction equation
[C:1]1([S:7][C@@H:8]2[O:25][C@H:24]([CH2:26][O:27]C(=O)C)[C@H:19]([O:20]C(=O)C)[C@H:14]([O:15]C(=O)C)[C@H:9]2[O:10]C(=O)C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:1]1([S:7][C@@H:8]2[O:25][C@H:24]([CH2:26][OH:27])[C@H:19]([OH:20])[C@H:14]([OH:15])[C@H:9]2[OH:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 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 a solution of thioglycoside 39 (1.10 g, 2.5 mmol) in 50 mL of MeOH is added K2CO3 in small portions, until the reaction mixture tested basic to pH paper (pH 11). The reaction mixture is stirred at room temperature for 15 min and then neutralized with Amberlite resin (acid form). The resin is removed by filtration and washed with MeOH (2×50 mL). The filtrates are concentrated and azeotroped from toluene to remove the residue MeOH to afford 1-deoxy-1-(phenylthio)-β-D-galactopyranose which is taken on to the next step without further purification.

Workup

  1. customThe resin is removed by filtration
  2. washwashed with MeOH (2×50 mL)
  3. concentrationThe filtrates are concentrated
  4. customazeotroped from toluene
  5. customto remove the residue MeOH

Sources & evidence

ORD record
ord-e0735cb059184dc4b657d100395554f5
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Reaction notes

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