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

HRID 1496820Notes

Reaction equation

HRID 1496820 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 108752501,3,4,5-Tetra-O-benzyl-D-glucitol

Product 1

HCID 110507692,3,4,6-Tetra-O-benzyl-1,5-di-O-mesyl-D-glucitol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

2,3,4,6-Tetra-O-benzyl-D-glucitol (45 g) was dissolved in pyridine (200 ml) and added over 30 min to a solution of mesyl chloride (15 ml) in pyridine (100 ml) at 0° C. The clear solution was stored at 4° C. overnight, after which time 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 a yellow/orange oil. The oil was azeotroped with toluene and 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 to a yellow/orange oil
  6. customThe oil was azeotroped with toluene

Sources & evidence

ORD record
ord-f55ecb3387b747ae9cb889f5978d326d
Source dataset
uspto-grants-2015_12
Patent number
US09199935B2

Reaction notes

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