Formic Acid → Phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranoside

HRID 610443Notes

Reaction equation

HRID 610443 reaction equation
[CH3:1][O:2][C:3]1[CH:64]=[CH:63][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@H:20]([O:32][CH2:33][C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[C@@H:19]([CH2:42][O:43]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[O:18][C@H:10]2[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:5][CH:4]=1.C(O)=O>CCOCC>[CH3:1][O:2][C:3]1[CH:64]=[CH:63][C:6]([CH2:7][O:8][C@@H:9]2[C@@H:21]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=3)[C@H:20]([O:32][CH2:33][C:34]3[CH:35]=[CH:36][C:37]([O:40][CH3:41])=[CH:38][CH:39]=3)[C@@H:19]([CH2:42][OH:43])[O:18][C@H:10]2[S:11][C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 284Formic AcidHCID 15433385Phenyl 2,3,4-tri-O-(4-methoxybenzyl)-6-O-triphenylmethyl-1-thio-beta-D-glucopyranoside

Product 1

HCID 15433386Phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-beta-D-glucopyranosideYield 51.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of phenyl 2,3,4-tri-O-(4-methoxybenzyl)-6-O-triphenylmethyl-1-thio-β-D-glucopyranoside (7) (3.44 g, 3.93 mmol) in ether (8 ml) was added formic acid (8 ml), and the resulting mixture was stirred at room temperature for 5 hr. The reaction mixture was washed successively with water, saturated aqueous sodium hydrogen-carbonate solution and saturated brine, and the solvent was evaporated under reduced pressure. The residue was suspended in a mixture of ethanol (5 ml) and 1N aqueous sodium hydroxide solution (5 ml), and the suspension was stirred overnight at room temperature. Ethanol was evaporated under reduced pressure and the resulting suspension was extracted twice with ether. The combined ether layers were washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue obtained was purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1) to give phenyl 2,3,4-tri-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (8) (1.28 g, yield 51%) as white crystals.

Workup

  1. washThe reaction mixture was washed successively with water, saturated aqueous sodium hydrogen-carbonate solution and saturated brine
  2. customthe solvent was evaporated under reduced pressure
  3. additionThe residue was suspended in a mixture of ethanol (5 ml) and 1N aqueous sodium hydroxide solution (5 ml)
  4. stirringthe suspension was stirred overnight at room temperature
  5. customEthanol was evaporated under reduced pressure
  6. extractionthe resulting suspension was extracted twice with ether
  7. washThe combined ether layers were washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue obtained
  11. customwas purified by silica gel column chromatography (eluent; hexane:ethyl acetate=2:1→1:1)

Sources & evidence

ORD record
ord-c6780d6fd8a74de7b802f20aa1e4dd8f
Source dataset
uspto-grants-1999_12
Patent number
US05998595

Reaction notes

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