((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

Base Information

Chemical Name:((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate
CAS No.:941694-72-0
Molecular Formula:C₁₆H₁₆O₅
Molecular Weight:288.3
Hs Code.:

Synonyms:((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

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Chemical Property of ((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

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Technology Process of ((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

There total 2 articles about ((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

: 941694-71-9
(3aR,6aR)-5-(hydroxymethyl)-2,2-dimethyl-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-4-one

: 98-88-4
benzoyl chloride

: 941694-72-0
((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

Guidance literature:: With pyridine; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/ja0688732

Reference yield:

: 115509-13-2
(3aR,6aR)-2,2-Dimethyl-3a,6a-dihydro-cyclopenta[1,3]dioxol-4-one

: 941694-72-0
((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 2 steps

1: 79 percent / imidazole / tetrahydrofuran; H₂O / 4 h / 0 °C

2: 86 percent / pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

With pyridine; 1H-imidazole; In tetrahydrofuran; dichloromethane; water; 1: Baylis-Hillman reaction;
DOI:10.1021/ja0688732

Reference yield:

: 941694-72-0
((3aR,6aR)-2,2-dimethyl-4-oxo-3a,6a-dihydrocyclopenta[1,2-d]1,3-dioxalan-5-yl)methyl benzoate

: rac-((4S,6S,1R,2R)-8-oxo-7,9-dioxa-8-thiatricyclo[4.3.0.0^2,4]non-4-yl)methyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1.1: 92 percent / CeCl₃*7H₂O; NaBH₄ / methanol / 0.5 h / 0 °C

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 92 percent / tetrahydrofuran / 0.5 h

3.1: 88 percent / AIBN; tri-n-butyltin hydride / toluene / 1.5 h / 120 °C

4.1: 75 percent / aq. AcOH / 1 h / 50 °C

5.1: 51 percent / diethylzinc / hexane; CH₂Cl₂ / 48 h / 20 °C

6.1: Et₃N; SOCl₂ / CH₂Cl₂ / 0.17 h / 0 °C

With sodium tetrahydroborate; thionyl chloride; cerium(III) chloride; 2,2'-azobis(isobutyronitrile); diethylzinc; tri-n-butyl-tin hydride; sodium hydride; acetic acid; triethylamine; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 5.1: Simmons-Smith cyclopropanation;
DOI:10.1021/ja0688732