3-Acetyldigoxigenin

Base Information

• Chemical Name: 3-Acetyldigoxigenin
• CAS No.: 80680-86-0
• Molecular Formula: C25H36 O6
• Molecular Weight: 432.557
• Mol file: 80680-86-0.mol

Synonyms:5b-Card-20(22)-enolide, 3b,12b,14-trihydroxy-, 3-acetate (7CI); Digoxigenin,3-acetate (6CI)

Chemical Property of 3-Acetyldigoxigenin

Chemical Property:

• Vapor Pressure: 2.19E-16mmHg at 25°C
• Boiling Point: 590.2°C at 760 mmHg
• Flash Point: 197.1°C
• PSA: 93.06000
• Density: 1.26g/cm³
• LogP: 3.14590

Purity/Quality:

99%min ^*data from raw suppliers

3-ACETYLDIGOXIGENIN 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Acetyldigoxigenin

There total 20 articles about 3-Acetyldigoxigenin 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: 74.0%

3β-Acetoxy-14-hydroxy-12-oxo-5β,14β-card-20(22)-enolid (2842-86-6) → 3β-Acetoxy-12β,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-86-0) + 3β-Acetoxy-12α,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-87-1)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; for 1h; Ambient temperature;

Reference yield: 44.0%

Acetic acid (2S,4aS,5S,6R,8aR)-4a-methyl-6-[(S)-2-methyl-3-(5-oxo-2,5-dihydro-furan-3-yl)-cyclopent-1-enyl]-5-(2-oxo-ethyl)-decahydro-naphthalen-2-yl ester (80680-88-2) → 3β-Acetoxy-12β,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-86-0) + 3β-Acetoxy-12α,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-87-1)

Guidance literature:

DOI:10.1016/S0040-4039(01)81912-2

Reference yield:

Deoxycholic acid (83-44-3) → 3β-Acetoxy-12β,14-dihydroxy-5β,14β-card-20(22)-enolid (80680-86-0)

Guidance literature:

Multi-step reaction with 10 steps

1: tetrahydrofuran / 3 h / Ambient temperature

2: tetrahydrofuran / 24 h / Ambient temperature; Irradiation

3: 73 percent / triphenylphosphane, EtOOC-N₂-COOEt / tetrahydrofuran / 70 h / Ambient temperature

4: 99 percent / 4-(dimethylamino)pyridine / pyridine / 16 h / Ambient temperature

5: 89 percent / 85percent m-chloroperbenzoic acid / CH₂Cl₂ / 2 h / Ambient temperature

6: 57 percent / Al-isopropylate / toluene / 5 h / Heating

7: 91 percent / MnO₂ / CH₂Cl₂ / 1 h / Ambient temperature

8: 1.) K-tert-C₄H₉; 2.) O₂, Bengalrosa B / <18>crown-6 / 1.) CH₂Cl₂, 4h, room temp.; 2.) CH₂Cl₂, 30 min, irradiation

9: 86 percent / pyridiniumchlorochromate, NaAc*3H₂O / CH₂Cl₂ / 0.42 h / Ambient temperature

10: 2.) CH₃COOH, CF₃COOH, H₂O / 1.) CH₂Cl₂, room temp., 30 min, irradiation; 2.) THF, 15 degC, 24h

With dmap; manganese(IV) oxide; water; oxygen; sodium acetate; rose bengal; aluminum isopropoxide; Kalium-tert-butylat; acetic acid; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; pyridinium chlorochromate; trifluoroacetic acid; diethylazodicarboxylate; 18-crown-6 ether; In tetrahydrofuran; pyridine; dichloromethane; toluene;

DOI:10.1002/jlac.198219821203

upstream raw materials:

Acetic acid (2S,4aS,5S,6R,8aR)-4a-methyl-6-[(S)-2-methyl-3-(5-oxo-2,5-dihydro-furan-3-yl)-cyclopent-1-enyl]-5-(2-oxo-ethyl)-decahydro-naphthalen-2-yl ester

3β-Acetoxy-12-oxo-5β,14α-card-20(22)-enolid

3β-Acetoxy-14-hydroxy-12-oxo-5β,14β-card-20(22)-enolid

3,12-Diacetyl-digoxingenin

Downstream raw materials:

digoxigenin

digoxigenin 3-O-acetyl-12-tosylate

Refernces

• 1、 Hammann, Peter E.,Habermehl, Gerhard G.. "Elimination Reactions and Rearrangement of 14β-Hydroxy-12-sulfonyloxy Steroids.". . p. 149 - 156. Retrieved 2007/10/02.
• 2、 Welzel, Peter,Stein, Hermann. "14β-HYDROXY STEROIDS-III. SYNTHESIS OF DIGOXIGENIN FROM DEOXYCHOLIC ACID". . p. 3385 - 3388. Retrieved 2007/10/02.