ChemicalBook CAS DataBase List tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate synthesis

8synthesis methods

Product Name:tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate
CAS Number:154026-95-6
Molecular formula:C15H26O6
Molecular Weight:302.36

(4R-Cis)-6-Hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester

124655-09-0

75-36-5

tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

154026-95-6

Tert-butyl (4R,6S)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate (1.0 g, 3.84 mmol) was dissolved in 10 mL of dichloromethane, and pyridine (0.9 g, 11.52 mmol) was added at room temperature and stirred for 30 min. Acetyl chloride (0.66 g, 8.45 mmol) was then added and stirring was continued at room temperature for 1 hour. After completion of the reaction, 10 mL of water was added to the mixture and the organic layer was separated by stirring for 10 minutes. The aqueous layer was extracted twice with 5 mL of dichloromethane, the organic layers were combined and washed with 10 mL of water to separate the organic layer. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to afford 0.98 g (86% yield) of the target product (4R,6S)-tert-butyl (4R,6S)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate as light pink crystals.

124655-09-0 Synthesis

124655-09-0
253 suppliers
$11.00/1g

75-36-5 Synthesis

75-36-5
576 suppliers
$17.92/100G

154026-95-6
265 suppliers
$9.00/5g

Yield:154026-95-6 86%

Reaction Conditions:

Stage #1:1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate with pyridine in dichloromethane at 20; for 0.5 h;
Stage #2:acetyl chloride in dichloromethane at 20; for 1 h;

Steps:

3.1 Step 1: Preparation of the compound of formula I-5 {tert-butyl 2-((4R,6S)-6-(acetoxymethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate}
The compound of formula (I-1){Tert-butyl 2 - ((4R, 6S) -6- (hydroxymethyl) -2,2-dimethyl-1,3-dioxan-4-yl) acetate}(1.0 g, 3.84 mmol, Jiangsu Alpha Pharmaceutical) was dissolved in 10 ml of methylene chloride (MC), pyridine (0.9 g, 11.52 mmol) was added at room temperature, and the mixture was stirred at room temperature for 30 minutes.Acetyl chloride (0.66 g, 8.45 mmol) was added and the mixture was stirred at room temperature for 1 hour. 10 ml of water was added to the reaction mixture, and the mixture was stirred for 10 minutes, and the organic layer was separated. After 5 ml of methylene chloride was extracted twice, 10 ml of water was added thereto, followed by stirringThe organic layer was separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and distilled under reduced pressure to obtain 0.98 g (yield: 86%) of the compound of the formula I-2 in the form of a pale pink crystal.

References:

Mirae Fine Chemical Co., Ltd.;Hwang, Sung-Kwan;Park, Sang-Hoo;Park, Chang-Ha;Yang, Joon-Ha KR2016/126700, 2016, A Location in patent:Paragraph 0161; 0162-0165

FullText

127-09-3 Synthesis