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

HRID 2210304Notes

Reaction equation

HRID 2210304 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-c6f51424d4084a929932a526d2c8cf04
Source dataset
uspto-grants-1995_10
Patent number
US05457227

Reaction notes

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