Pavoninin 1

Base Information

• Chemical Name: Pavoninin 1
• CAS No.: 94426-01-4
• Molecular Formula: C₃₇H₅₉NO₉
• Molecular Weight: 661.877
• Mol file: 94426-01-4.mol

Synonyms:

Chemical Property of Pavoninin 1

Chemical Property:

• Vapor Pressure: 7.19E-30mmHg at 25°C
• Boiling Point: 803.5°Cat760mmHg
• Flash Point: 439.7°C
• PSA: 151.62000
• Density: 1.21g/cm³
• LogP: 4.46980

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Pavoninin 1

There total 17 articles about Pavoninin 1 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: 82.0%

C43H65NO9Se (202462-26-8) → pavoninin-1 (89936-15-2,94426-01-4)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; for 1h; Ambient temperature;

DOI:10.1016/S0968-0896(97)00170-3

Reference yield:

chenodeoxycholic acid (474-25-9) → pavoninin-1 (89936-15-2,94426-01-4)

Guidance literature:

Multi-step reaction with 17 steps

1: 88 percent / 4-dimethylaminopyridine, pyridine / 4 h / Ambient temperature

2: 1.) Pb(OAc)4, 2.) I₂ / 1.) CCl₄, irradiation, reflux, 20 min, 2.) CCl₄, reflux, 70 min

3: 90 percent / DMSO, 2,4,6-collidine / 1.5 h / 150 °C

4: 1.) NaN(SiMe₃)2 / 1.) THF, RT, 30 min, 2.) THF, 0 deg C, 1 h

5: 92 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

6: dimethylformamide / 17 h / Ambient temperature

7: H₂ / Pd(OH)2/C / ethanol / 96 h

8: 95 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

9: 1.) 2,6-di-tert-butyl-4-methylpyridine, triflic anhydride / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, from -78 deg C to -20 deg C

10: 96 percent / 46percent aq. HF / acetonitrile / 3.5 h / Ambient temperature

11: 95 percent / pyridinium dichromate, molecular sieves 4A / CH₂Cl₂ / 4.7 h / Ambient temperature

12: 96 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 2 h / Ambient temperature

13: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

14: DMAP, pyridine / 4 h / Ambient temperature

15: 87 percent / H₂ / Pd(OH)2/C / methanol / 20 h / Ambient temperature

16: 30 percent / ethyl acetate / 2 h / Ambient temperature

17: 82 percent / 30percent aq. H₂O₂ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; lead(IV) acetate; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; hydrogen; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; dimethyl sulfoxide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(97)00170-3

Reference yield:

3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid (33628-52-3) → pavoninin-1 (89936-15-2,94426-01-4)

Guidance literature:

Multi-step reaction with 16 steps

1: 1.) Pb(OAc)4, 2.) I₂ / 1.) CCl₄, irradiation, reflux, 20 min, 2.) CCl₄, reflux, 70 min

2: 90 percent / DMSO, 2,4,6-collidine / 1.5 h / 150 °C

3: 1.) NaN(SiMe₃)2 / 1.) THF, RT, 30 min, 2.) THF, 0 deg C, 1 h

4: 92 percent / LiAlH₄ / tetrahydrofuran / 2 h / Ambient temperature

5: dimethylformamide / 17 h / Ambient temperature

6: H₂ / Pd(OH)2/C / ethanol / 96 h

7: 95 percent / pyridine / CH₂Cl₂ / 4 h / 0 °C

8: 1.) 2,6-di-tert-butyl-4-methylpyridine, triflic anhydride / 1.) CH₂Cl₂, -78 deg C, 5 min, 2.) CH₂Cl₂, from -78 deg C to -20 deg C

9: 96 percent / 46percent aq. HF / acetonitrile / 3.5 h / Ambient temperature

10: 95 percent / pyridinium dichromate, molecular sieves 4A / CH₂Cl₂ / 4.7 h / Ambient temperature

11: 96 percent / camphorsulfonic acid / CH₂Cl₂; methanol / 2 h / Ambient temperature

12: LiAlH₄ / tetrahydrofuran / 6 h / Ambient temperature

13: DMAP, pyridine / 4 h / Ambient temperature

14: 87 percent / H₂ / Pd(OH)2/C / methanol / 20 h / Ambient temperature

15: 30 percent / ethyl acetate / 2 h / Ambient temperature

16: 82 percent / 30percent aq. H₂O₂ / tetrahydrofuran / 1 h / Ambient temperature

With pyridine; 2,4,6-trimethyl-pyridine; lead(IV) acetate; dmap; lithium aluminium tetrahydride; dipyridinium dichromate; 2,6-di-tert-butyl-4-methylpyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; camphor-10-sulfonic acid; hydrogen fluoride; hydrogen; dihydrogen peroxide; iodine; sodium hexamethyldisilazane; dimethyl sulfoxide; palladium dihydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0968-0896(97)00170-3

upstream raw materials:

C₄₃H₆₅NO₉Se

chenodeoxycholic acid

3α,7α-diacetoxy-24-phenyl-5β-cholan-24-oic acid

23-iodo-24-nor-5β-cholane-3α,7α-diyl diacetate

Downstream raw materials:

coprostanone

Refernces