Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 14803011, compound

HRID 1641520Notes

Reaction equation

HRID 1641520 reaction equation
O1CCCCC1[C:7]1([S:37][C@H:36]([CH2:38][O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C@@H:27]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:9]1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[OH:8].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[CH2:11]([O:10][C@@H:9]1[C@@H:18]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@H:27]([O:28][CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C@@H:36]([CH2:38][O:39][CH2:40][C:41]2[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=2)[S:37][CH:7]1[OH:8])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 131728756HCID 131728756, compound

Product 1

HCID 14803011HCID 14803011, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of tetrahydro-2H-pyran-2-yl 2,3,4,6-tetra-O-benzyl-5-thio-D-glucopyranose (3.30 g, 5.15 mmoL), pyridinium p-toluenesulfonate (518 mg, 2.06 mmoL) and ethanol (58 mL) was stirred at 80° C. for 2 hours. The reaction mixture was cooled to room temperature and the solvent was concentrated. The resulting residue was dissolved in ethyl acetate. This solution was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride, and then dried over anhydrous magnesium sulfate. After filtering off the desiccant, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to give the titled compound (2.89 g, quant.) as a colorless crystal.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationthe solvent was concentrated
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. washThis solution was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtering off the desiccant
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-fc290478ecb14d399d03985bebac9cd4
Source dataset
uspto-grants-2012_02
Patent number
US08115017B2

Reaction notes

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