4-Toluenesulfonyl chloride → 1,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)

HRID 54824Notes

Reaction equation

HRID 54824 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C@@H:11]2[C@@H:15]([OH:16])[C@H:14]([CH2:17][OH:18])[O:13][CH2:12]2)=[CH:5][CH:4]=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1>N1C=CC=CC=1>[CH3:29][C:19]1[CH:24]=[CH:23][C:22]([S:25]([O:18][CH2:17][C@@H:14]2[O:13][CH2:12][C@H:11]([S:10][CH2:9][C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C@H:15]2[OH:16])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 67648335HCID 67648335, compound

Product 1

HCID 883371051,4-Anhydro-2-S-[(4-methoxyphenyl)methyl]-2-thio-L-arabinitol 5-(4-Methylbenzenesulfonate)Yield 57.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0° C. solution, under argon, of 0.580 g of product from Example 323 in 10 ml of pyridine is added 0.430 g of p-toluenesulfonyl chloride. The reaction is stirred at room temperature overnight. The mixture is quenched with water, extracted with diethyl ether, washed with water and saturated sodium chloride, dried and concentrated in vacuo. The residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane) to give 0.520 g of the desired product.

Workup

  1. customThe mixture is quenched with water
  2. extractionextracted with diethyl ether
  3. washwashed with water and saturated sodium chloride
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by chromatography (Silica gel: 50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-7c9d57332bb745b8b732ffbda4067521
Source dataset
uspto-grants-1997_04
Patent number
US05623081

Reaction notes

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