Potassium Carbonate → HCID 54499710, compound

HRID 1637415Notes

Reaction equation

HRID 1637415 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]([CH3:26])[O:14][CH:6]1[S:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)(=O)C.C([O-])([O-])=O.[K+].[K+]>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]([CH3:26])[C@@H:16]([OH:22])[C@@H:17]([OH:18])[C@@H:5]1[OH:4]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 21970480HCID 21970480, compound

Product 1

HCID 54499710HCID 54499710, compoundYield 232.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of phenyl 6-deoxy-2,3,4-tri-O-acetyl-1-thio-β-L-galactopyranoside 2 (0.892 g, 2.33 mmol) in 25 mL of methanol is added K2CO3 (0.644 g, 4.66 mmol). The reaction mixture is stirred at room temperature for 12 h. Amberlite resin (H+ form) is added to the reaction mixture and stirred for an additional 30 min. The neutralized mixture is then filtered through Celite, which is washed several times with methanol, and the filtrate is concentrated to afford 1.39 g of phenyl 6-deoxy-1-thio-β-L-galactopyranoside 3 as a yellow oil, which is used in the next step without further purification. The thioglycoside 3 can be purified using flash chromatography (10% MeOH/CH2Cl2): Rf 0.28 (10% MeOH/CH2Cl2); 1H NMR (C6D6, 270 MHz) δ 7.54-7.58 (m, 2H) 7.28-7.37 (m, 3H), 4.50 (d, J=8.2 Hz, 1H, H-1), 3.70 (q, J=6.6 Hz, 1H, H-5), 3.56-3.75 (m, 3H), 1.38 (d, J=6.6 Hz, 3H).

Workup

  1. additionAmberlite resin (H+ form) is added to the reaction mixture
  2. stirringstirred for an additional 30 min
  3. filtrationThe neutralized mixture is then filtered through Celite, which
  4. washis washed several times with methanol
  5. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-5f898c4ae42347bc9a8f78a6380f8af1
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Reaction notes

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