Methanesulfonyl chloride → 2,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-galactitol

HRID 1496822

Reaction equation

HRID 1496822 reaction equation
[CH2:1]([O:8][C@H:9]([C@H:12]([C@H:21]([C@@H:30]([CH2:32][O:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[OH:31])[O:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S:41](Cl)([CH3:44])(=[O:43])=[O:42]>N1C=CC=CC=1>[CH2:1]([O:8][C@H:9]([C@H:12]([C@H:21]([C@@H:30]([CH2:32][O:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[O:31][S:41]([CH3:44])(=[O:43])=[O:42])[O:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[CH2:10][O:11][S:41]([CH3:44])(=[O:43])=[O:42])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 100075242,3,4,6-Tetrakis-O-(phenylmethyl)-D-galactitol

Product 1

HCID 117873332,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-galactitol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2,3,4,6-Tetra-O-benzyl-D-galactitol (7.6 g) was stirred at 0° C. in pyridine (20 ml) and a solution of mesyl chloride (2.5 ml) in pyridine (20 ml) was added. The solution was stored at 4° C. overnight. TLC analysis showed completion of the reaction. The reaction mixture was partitioned between ethyl acetate and water/ice. The organic fractions were washed with 5% hydrochloric acid then saturated aqueous sodium bicarbonate solution, dried (Na2SO4) and concentrated to give a colourless oil which was used directly in the next stage.

Workup

  1. customcompletion of the reaction
  2. customThe reaction mixture was partitioned between ethyl acetate and water/ice
  3. washThe organic fractions were washed with 5% hydrochloric acid
  4. dry with materialsaturated aqueous sodium bicarbonate solution, dried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a colourless oil which

Sources & evidence

ORD record
ord-2c5aef204fb6403eb2fbf7d63cedc863
Source dataset
uspto-grants-2015_12
Patent number
US09199935B2

Linked notes

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