Sodium Iodide → 1-Desoxy-1-iodo-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranose

HRID 234607Notes

Reaction equation

HRID 234607 reaction equation
C1(C)C=CC(S([CH:10]([C@:12]2([O:23][CH2:22][C@@H:19]([O:20][CH3:21])[C@@H:16]([O:17][CH3:18])[C@@:14]2([C:24]([CH3:26])=[CH2:25])[OH:15])[OH:13])O)(=O)=O)=CC=1.[I-:28].[Na+]>CC(C)=O.C(OCC)C.CCCCC>[I:28][CH2:10][C@:12]1([O:23][CH2:22][C@@H:19]([O:20][CH3:21])[C@@H:16]([O:17][CH3:18])[C@@:14]1([C:24]([CH3:26])=[CH2:25])[OH:15])[OH:13]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 544128151-para-Toluenesulfonyl-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranos

Product 1

HCID 867502171-Desoxy-1-iodo-3-isopropenyl-4,5-di-O-methyl-beta-D-psicopyranoseYield 88%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 21877078Diethylether pentaneSolvent

Procedure

Following the procedure described for the preparation of Example 12, starting from 0.10 g (0.25 mmol) of the compound obtained in Example 30 and 0.18 g (1.20 mmol) of sodium iodide in 3 ml of acetone at room temperature, then purification by chromatography on silica gel (eluant: diethyl ether/pentane, 1.5:1), 0.079 g (0.22 mmol) of the desired product in the form of a pale-yellow-coloured solid is obtained.

Workup

  1. customdescribed for the preparation of Example 12

Sources & evidence

ORD record
ord-e54263faa9a44790b76fd9dc4b236ec2
Source dataset
uspto-grants-1997_01
Patent number
US05595976

Reaction notes

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