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

HRID 909768Notes

Reaction equation

HRID 909768 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 two hours. The reaction mixture was cooled to room temperature and the solvent was concentrated. The obtained residue was dissolved in ethyl acetate. After this solution was washed with a saturated sodium bicarbonate aqueous solution and brine, it was dried with anhydrous magnesium sulfate. After the desiccant was filtered off, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1) to obtain 2,3,4,6-tetra-O-benzyl-5-thio-D-glucopyranose (2.89 g, quant) as a colorless crystal. 13C NMR (125 MHz, CHLOROFORM-d) δ 41.3, 67.8, 71.6, 73.0, 73.2, 75.6, 76.2, 81.9, 82.9, 84.4, 127.5, 127.7, 127.8, 127.9, 128.0, 128.3, 128.4, 128.5, 137.8, 138.3, 138.8.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationthe solvent was concentrated
  3. dissolutionThe obtained residue was dissolved in ethyl acetate
  4. washAfter this solution was washed with a saturated sodium bicarbonate aqueous solution and brine, it
  5. dry with materialwas dried with anhydrous magnesium sulfate
  6. filtrationAfter the desiccant was filtered off
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-6113abb73e104a998d9bca83f95f89ac
Source dataset
uspto-grants-2011_09
Patent number
US08017792B2

Reaction notes

Loading…