22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide

Base Information

• Chemical Name: 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide
• CAS No.: 332949-32-3
• Molecular Formula: C₃₇H₄₂O₇
• Molecular Weight: 598.736
• Mol file: 332949-32-3.mol

Synonyms:22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide

Chemical Property of 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide

There total 3 articles about 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide 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: 94.0%

22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide (332949-17-4) → 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide (332949-32-3)

Guidance literature:

22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide; With toluene-4-sulfonic acid; In methanol; at 20 ℃; for 24h;

With hydrogenchloride; In 1,4-dioxane; at 40 ℃; for 6h;

DOI:10.1016/S0040-4020(00)00916-9

Reference yield:

4-carboxybenzophenone (611-95-0) → 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide (332949-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / 4-dimethylaminopyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 4 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / methanol / 24 h / 20 °C

2.2: 94 percent / aq. HCl / dioxane / 6 h / 40 °C

With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1.1: Esterification / 2.1: desilylation; acetalization / 2.2: Hydrolysis;

DOI:10.1016/S0040-4020(00)00916-9

Reference yield:

4-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-3-hydroxy-5H-furan-2-one (182573-89-3) → 22-(4-benzoylbenzoyloxy)-3β,14-dihydroxy-5β,14β-card-20(22)-enolide (332949-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 90 percent / 4-dimethylaminopyridine; N,N'-dicyclohexylcarbodiimide / CH₂Cl₂ / 4 h / 20 °C

2.1: p-toluenesulfonic acid monohydrate / methanol / 24 h / 20 °C

2.2: 94 percent / aq. HCl / dioxane / 6 h / 40 °C

With dmap; toluene-4-sulfonic acid; dicyclohexyl-carbodiimide; In methanol; dichloromethane; 1.1: Esterification / 2.1: desilylation; acetalization / 2.2: Hydrolysis;

DOI:10.1016/S0040-4020(00)00916-9

upstream raw materials:

22-(4-benzoylbenzoyloxy)-3β-(tert-butyldimethylsilyloxy)-14-trimethylsilyloxy-5β,14β-card-20(22)-enolide

4-carboxybenzophenone

4-[(3S,5R,8R,9S,10S,13R,14S,17S)-3-(tert-Butyl-dimethyl-silanyloxy)-10,13-dimethyl-14-trimethylsilanyloxy-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-3-hydroxy-5H-furan-2-one

Downstream raw materials:

22-(4-benzoylbenzoyloxy)-14-hydroxy-3β-(4-isothiocyanatobenzoyloxy)-5β,14β-card-20(22)-enolide