Sodium Methoxide → HCID 53958828, compound

HRID 1637418Notes

Reaction equation

HRID 1637418 reaction equation
C([O:9][C@H:10]1[C@@H:22]([O:23]C(=O)C2C=CC=CC=2)[C@H:21]([CH3:32])[O:20][C@H:12]([S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:11]1[O:33][CH2:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][CH3:42])=[CH:37][CH:36]=1)(=O)C1C=CC=CC=1.C[O-].[Na+]>CO>[CH3:42][O:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][O:33][C@H:11]2[C@@H:10]([OH:9])[C@@H:22]([OH:23])[C@H:21]([CH3:32])[O:20][C@@H:12]2[S:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 54530788HCID 54530788, compound

Product 1

HCID 53958828HCID 53958828, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of crude phenyl 6-deoxy-3,4-di-O-benzoyl-2-O-(4-methoxybenzyl)-1-thio-β-L-allopyranoside β-13 in 20 mL of MeOH is added NaOMe (200 mg, 3.8 mmol). The reaction mixture is stirred at room temperature for 2 h and then neutralized with Amberlite resin. The solution is filtered, washed several times with MeOH and concentrated in vacua. The crude product is purified by flash chromatography (60% EtOAc/petroleum ether) to afford 1.01 g (72%, 3 steps) of phenyl 6-deoxy-2-O-(4-methoxybenzyl)-1-thio-β-L-allopyranoside (β-14): Rf 0.35 (50% EtOAc/petroleum ether); 1H NMR (CDCl3, 270 MHz) δ 7.56-7.52 (m, 2H, ArH), 7.31-7.27 (m, 5H, ArH), 6.89-6.88 (m, 2H, ArH), 4.93 (d, J=9.9 Hz, 1H, H-1), 4.71 (d, J=11.2 Hz, 1H, CH2), 4.55 (d, J=11.2 Hz, 1H, CH2), 4.13 (t, J=2.6 Hz, 1H, H-3), 3.83 (s, 3H, OCH3), 3.73-3.63 (m, 1H, H-5), 3.38 (dd, J=3.3, 9.9 Hz, 1H, H-2), 3.21 (dt, J=3.3, 9.6 Hz, 1H, H-4), 2.58 (s, 1H, OH) 2.34-2.30 (d, 1H, OH), 1.33 (d, J=6.3 Hz, 3H, H-6).

Workup

  1. filtrationThe solution is filtered
  2. washwashed several times with MeOH
  3. concentrationconcentrated in vacua
  4. customThe crude product is purified by flash chromatography (60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-4e77bf0ca45c4fdd9c1e8d9118c7209e
Source dataset
uspto-grants-2000_03
Patent number
US06040433

Reaction notes

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