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154026-95-6

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Basic Information
CAS No.: 154026-95-6
Name: tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate
Article Data: 12
Molecular Structure:
Molecular Structure of 154026-95-6 (tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate)
Formula: C15H26O6
Molecular Weight: 302.368
Synonyms: Rosuvastatin calcium intermediate C-1;(4R-Cis)-6-[(Acetyloxy methyl)]-2,2-Dimethyl-1,3-Dioxane -4-Acetic Acid,1,1-Dimethyethyl Ester;(4R-Cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester(D5);
EINECS: 688-142-5
Density: 1.037 g/cm3
Boiling Point: 353.142 °C at 760 mmHg
Flash Point: 150.334 °C
Appearance: White or off-white solid powder
PSA: 71.06000
LogP: 2.19150
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Synthetic route
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tetrabutylammonium acetate

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
at 115℃; for 7h;99.1%
In 1-methyl-pyrrolidin-2-one at 25 - 95℃; for 24h;7.2 g
127-09-3

sodium acetate

154026-94-5

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
With copper(l) chloride In N,N-dimethyl-formamide at 120 - 130℃; for 24h; Reagent/catalyst; Solvent;97.6%
With tetrabutylammomium bromide In N,N-dimethyl-formamide at 120℃; for 4h; Solvent;542.97 g

(3R,5S)-6-acetoxy-3,5-dihydroxyhexanoic acid tert-butyl ester

77-76-9

2,2-dimethoxy-propane

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
With methanesulfonic acid In toluene at 20℃; for 8h;95.8%
With methanesulfonic acid In toluene at 0 - 5℃; for 4h;88.1%
124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

75-36-5

acetyl chloride

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate With pyridine In dichloromethane at 20℃; for 0.5h;
Stage #2: acetyl chloride In dichloromethane at 20℃; for 1h;		86%
With pyridine In dichloromethane at 20℃; for 0.5h;15.9 g
631-61-8

ammonium acetate

154026-94-5

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 95℃; for 24h;80%
127-08-2

potassium acetate

154026-94-5

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
Stage #1: potassium acetate; (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester With tetrabutyl phosphonium bromide In toluene at 105℃; for 22h;
Stage #2: With pyrographite In n-heptane; toluene at 20℃;		76%
Stage #1: (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester; 1-ethyl-3-methylimidazolium acetate at 90℃; for 5h;
Stage #2: potassium acetate at 90℃; for 23.5h; Product distribution / selectivity;
In 1-ethyl-3-methyl-1H-imidazol-3-ium chloride at 110℃; for 2.5h;

(3R,5S) t-butyl 6-acetoxy-3,5-dihydroxyhexanoate

144-55-8

sodium hydrogencarbonate

77-76-9

2,2-dimethoxy-propane

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
With toluene-4-sulfonic acid In dichloromethane; ethyl acetate
...Expand
chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

chloride (4R-cis)-6-(chloromethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid, 1,1-dimethylethyl ester

10534-59-5

tetrabutylammonium acetate

124655-09-0

1,1-dimethylethyl (4R-cis)-6-hydroxymethyl-2,2-dimethyl-1,3-dioxane-4-acetate

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one
...Expand
127-08-2

potassium acetate

143314-17-4

1-ethyl-3-methylimidazolium acetate

154026-94-5

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
at 100℃; for 4h;
...Expand
143314-17-4

1-ethyl-3-methylimidazolium acetate

154026-94-5

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

154026-95-6

(4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester

Conditions
ConditionsYield
at 100℃; for 3h; Product distribution / selectivity;
Raw Materials
154026-94-5
75-36-5
143314-17-4
127-08-2
10534-59-5
124655-09-0
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124655-09-0
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  • tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate

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    154026-95-6

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

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  • D-5: (4R-Cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester

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    D-5: (4R-Cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid,1,1-dimethylethyl ester

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Chemistry

Empirical Formula of tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate (CAS NO.154026-95-6): C15H26O6
Molecular Weight: 302.3633
Nominal Mass: 302 Da
Average Mass: 302.3633 Da
Monoisotopic Mass: 302.172939 Da 
Index of Refraction: 1.436
Molar Refractivity: 76.312 cm3
Molar Volume: 291.645 cm3
Surface Tension: 33.982 dyne/cm
Density: 1.037 g/cm3
Flash Point: 150.334 °C
Enthalpy of Vaporization: 59.804 kJ/mol
Boiling Point: 353.142 °C at 760 mmHg
Structure of tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate (CAS NO.154026-95-6):
                              
Systematic Name: tert-Butyl 6-O-acetyl-2,4-dideoxy-3,5-O-(1-methylethylidene)-D-erythro-hexonate
SMILES: O=C(OC(C)(C)C)C[C@@H]1OC(O[C@@H](C1)COC(=O)C)(C)C 
InChI: InChI=1/C15H26O6/c1-10(16)18-9-12-7-11(19-15(5,6)20-12)8-13(17)21-14(2,3)4/h11-12H,7-9H2,1-6H3/t11-,12+/m1/s1 
InChIKey: NGABCYSYENPREI-NEPJUHHUBW
Std. InChI: InChI=1S/C15H26O6/c1-10(16)18-9-12-7-11(19-15(5,6)20-12)8-13(17)21-14(2,3)4/h11-12H,7-9H2,1-6H3/t11-,12+/m1/s1 
Std. InChIKey: NGABCYSYENPREI-NEPJUHHUSA-N

Specification

 tert-Butyl (4R-cis)-6-[(acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetate (CAS NO.154026-95-6) also can be called (4R-cis)-6-[(Acetyloxy)methyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester .