Potassium Carbonate → tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

HRID 234175Notes

Reaction equation

HRID 234175 reaction equation
C([O:9][CH2:10][C@H:11]1[O:16][C:15]([CH3:18])([CH3:17])[O:14][C@@H:13]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1)(=O)C1C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:9][CH2:10][C@H:11]1[O:16][C:15]([CH3:17])([CH3:18])[O:14][C@@H:13]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:12]1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 101333842-[(4R, 6S)-2,2-dimethyl-6-benzoyloxymethyl-1,3-dioxan-4-yl]acetic tert-butyl ester

Product 1

HCID 9816650tert-Butyl 2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (4R-cis)-6-[(benzoyloxy)methyl]-2,2-dimethyl-1,3 -dioxane-4-acetic acid, 1,1-dimethylethyl ester prepared in step (a) above (30.00 g, 82.4 mmole) in methanol (275 ml) was added granular anhydrous potassium carbonate (5.68 g, 41.2 mmole) in one portion. The resulting heterogeneous solution was stirred vigorously for 2 hours to complete the hydrolysis. The progress of the reaction was followed by TLC analysis. (TLC: Rf =0.31 for the benzoyloxy starting material, Rf =0.17 for the title compound (silica gel, Ether:Hexane, 1:1, visualized by Ce(SO4)2 spray).

Workup

  1. customthe hydrolysis

Sources & evidence

ORD record
ord-65a36c272ea8490dbddc693d1b82728f
Source dataset
uspto-grants-1997_01
Patent number
US05594153

Reaction notes

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