Methanesulfonyl chloride → 3,5-di-O-benzyl-2-deoxy-4-O-methane-sulphonyl-L-threo-pentose dibenzyl dithioacetal

HRID 440712Notes

Reaction equation

HRID 440712 reaction equation
[CH2:1]([S:8][CH:9]([S:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[CH2:10][C@@H:11]([C@H:20]([CH2:22][O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[OH:21])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:39][S:40](Cl)(=[O:42])=[O:41]>N1C=CC=CC=1>[CH2:32]([S:31][CH:9]([S:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:10][C@@H:11]([C@H:20]([CH2:22][O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[O:21][S:40]([CH3:39])(=[O:42])=[O:41])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 150599573,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal

Product 1

HCID 150599603,5-di-O-benzyl-2-deoxy-4-O-methane-sulphonyl-L-threo-pentose dibenzyl dithioacetal

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 3,5-di-O-benzyl-2-deoxy-L-threo-pentose dibenzyl dithioacetal (61.4 g, 113 mmol) in dry pyridine (700 ml) was added methanesulphonyl chloride (19.4 g, 169 mmol) in dry pyridine (200 ml) dropwise, with stirring, at 0° C. The temperature of the mixture was raised to room temperature and stirring continued for 18 hours. The pyridine was then removed in vacuo and the residue dissolved in dichloromethane. The dichloromethane extracts were then successively washed with 2M hydrochloric acid, 1M sodium carbonate and water, dried (magnesium sulphate) and evaporated to give the title product as a thick viscous syrup. A sample of this was crystallised from hexane-ethyl acetate to give the title product as white crystals, m.p 82°-83° C.

Workup

  1. temperatureThe temperature of the mixture was raised to room temperature
  2. stirringstirring
  3. customThe pyridine was then removed in vacuo
  4. dissolutionthe residue dissolved in dichloromethane
  5. washThe dichloromethane extracts were then successively washed with 2M hydrochloric acid, 1M sodium carbonate and water
  6. dry with materialdried (magnesium sulphate)
  7. customevaporated

Sources & evidence

ORD record
ord-c9b256705bed443288b6f29296ee4bdd
Source dataset
uspto-grants-1996_05
Patent number
US05521163

Reaction notes

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