(7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Base Information

• Chemical Name: (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane
• CAS No.: 1402852-48-5
• Molecular Formula: C₂₃H₂₃ClO₈
• Molecular Weight: 462.884

Synonyms:(7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Chemical Property of (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Chemical Property:

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Technology Process of (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

There total 3 articles about (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane 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:

5-[(3-chlorophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (15948-53-5) + 6,6-dimethyl-2-ethenyl-5,7-dioxaspiro[2.5]octane-4,8-dione (57742-53-7,71107-18-1) → (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane (1402852-48-5) + (7R,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In 1,4-dioxane; at 20 ℃; for 16.8333h; Overall yield = 65%; Overall yield = 59.7 mg; enantioselective reaction; Inert atmosphere;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

Reference yield:

cycl-isopropylidene malonate (2033-24-1) → (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane (1402852-48-5) + (7R,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

1.2: 19 h / 0 - 20 °C / Inert atmosphere

2.1: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane / 1,4-dioxane / 16.83 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; potassium carbonate; (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

Reference yield:

cycl-isopropylidene malonate (2033-24-1) + m-Chlorobenzaldehyde (587-04-2) → (7R,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane (1402852-48-5) + (7R,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14R)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane + (7S,14S)-1,5,9,13-tetraoxy-3,3,11,11-tetramethyl-7-(3-chlorophenyl)-14-vinyl-2,4,10,12-tetraoxadispiro[5.1.5.2]pentadecane

Guidance literature:

Multi-step reaction with 2 steps

1: pyrrolidine acetic acid / benzene / 16 h / Inert atmosphere; Reflux

2: tris(dibenzylideneacetone)dipalladium(0) chloroform complex; (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane / 1,4-dioxane / 16.83 h / 20 °C / Inert atmosphere

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; pyrrolidine acetic acid; (-)-1(R),2(R)-bis<2'-(diphenylphosphino)benzamido>-1,2-diphenylethane; In 1,4-dioxane; benzene;

DOI:10.1021/ja309003x DOI:10.1021/ja309003x

upstream raw materials:

5-[(3-chlorophenyl)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione

6,6-dimethyl-2-ethenyl-5,7-dioxaspiro[2.5]octane-4,8-dione

cycl-isopropylidene malonate

m-Chlorobenzaldehyde

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