4-Toluenesulfonyl chloride → 1-para-Toluenesulfonyl-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranos

HRID 234606Notes

Reaction equation

HRID 234606 reaction equation
[C:1]([C@@:4]1([OH:17])[C@H:12]([O:13][CH3:14])[C@H:11]([O:15][CH3:16])[CH2:10][O:9][C@:5]1([OH:8])[CH2:6][OH:7])([CH3:3])=[CH2:2].[S:18](Cl)([C:21]1[CH:27]=[CH:26][C:24]([CH3:25])=[CH:23][CH:22]=1)(=[O:20])=[O:19]>N1C=CC=CC=1.C(OCC)C.CCCCC>[C:24]1([CH3:25])[CH:26]=[CH:27][C:21]([S:18]([CH:6]([C@:5]2([O:9][CH2:10][C@@H:11]([O:15][CH3:16])[C@@H:12]([O:13][CH3:14])[C@@:4]2([C:1]([CH3:3])=[CH2:2])[OH:17])[OH:8])[OH:7])(=[O:20])=[O:19])=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 536958503-Isopropenyl-4,5-di-O-methyl-beta-D-psicopyranose

Product 1

HCID 544128151-para-Toluenesulfonyl-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranosYield 70.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 21877078Diethylether pentaneSolvent

Procedure

Following the procedure described for the preparation of Example 10, starting from 0.80 g (3.22 mmol) of the compound obtained in Example 29 and 1.53 g of tosyl chloride in 15 ml of anhydrous pyridine, then purification by chromatography on silica gel (eluant: diethyl ether/pentane, 2:1), 0.92 g (2.28 mmol) of the desired product in the form of a white-coloured foam is obtained.

Workup

  1. customdescribed for the preparation of Example 10

Sources & evidence

ORD record
ord-3ea937f0093f4073bbd3b1a6655a5040
Source dataset
uspto-grants-1997_01
Patent number
US05595976

Reaction notes

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