[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

Base Information

Chemical Name:[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate
CAS No.:474958-88-8
Molecular Formula:C₂₄H₂₆O₄
Molecular Weight:378.468
Hs Code.:

Synonyms:[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

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Chemical Property of [(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

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Technology Process of [(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

There total 7 articles about [(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate 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: 73.0%

: 140-10-3
(E)-3-phenylacrylic acid

: 1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-en-1-ol

: 474958-88-8
[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo0259358

Reference yield:

: 202589-95-5
(1S,2S)-1-phenyl-but-3-ene-1,2-diol

: 474958-88-8
[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: PPTS / CH₂Cl₂ / 1 h

2.1: OsO₄; NMO / acetone; H₂O / 6 h / 20 °C

2.2: NaIO₄ / H₂O; acetone / 0.5 h / 25 °C

3.1: diethyl ether; pentane / 2 h / -100 °C

3.2: 73 percent / NaOH; H₂O₂ / diethyl ether; pentane; H₂O / 4 h / 20 °C

4.1: 73 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In diethyl ether; dichloromethane; water; acetone; pentane;
DOI:10.1021/jo0259358

Reference yield:

: 100-52-7
benzaldehyde

: 474958-88-8
[(1R)-1-((4S,5S)-2,2-dimethyl-5-phenyl-[1,3]-dioxolan-4-yl)-but-3-enyl]-3-phenyl prop-2-enoate

Guidance literature:: Multi-step reaction with 7 steps

1.1: tetrahydrofuran / 2 h / -100 °C

2.1: 42.8 g / NaOH; H₂O₂ / tetrahydrofuran; H₂O / 10 h / 25 °C

3.1: conc. HCl / methanol / 5 h / 25 °C

4.1: PPTS / CH₂Cl₂ / 1 h

5.1: OsO₄; NMO / acetone; H₂O / 6 h / 20 °C

5.2: NaIO₄ / H₂O; acetone / 0.5 h / 25 °C

6.1: diethyl ether; pentane / 2 h / -100 °C

6.2: 73 percent / NaOH; H₂O₂ / diethyl ether; pentane; H₂O / 4 h / 20 °C

7.1: 73 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

With hydrogenchloride; dmap; sodium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; dihydrogen peroxide; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetone; pentane;
DOI:10.1021/jo0259358