11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β

Base Information

• Chemical Name: 11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β
• CAS No.: 30954-21-3
• Molecular Formula: C₂₇H₄₂O₁₁
• Molecular Weight: 542.624
• Mol file: 30954-21-3.mol

Synonyms:(3α,5α,11β)-11,17,21-trihydroxy-20-oxopregnan-3-yl β-D-Glucopyranosiduronic Acid;11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β;5α-Tetrahydrocortisol-3-Monoglucuronide;Allo-3α-tetrahydro Cortisol 3-O-β-D-Glucuronide;Allotetrahydrocortisol 3-Glucuronide

Chemical Property of 11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β

Chemical Property:

• Boiling Point: 768.2±60.0 °C(Predicted)
• PKA: 2.82±0.70(Predicted)
• PSA: 194.21000
• Density: 1.46±0.1 g/cm3(Predicted)
• LogP: -0.43020

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The 3-monoglucuronide conjugate of Allo-3α-tetrahydrocortisol (A548500).

Technology Process of 11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β

There total 12 articles about 11β,17,21-trihydroxy-20-oxo-5α-pregnan-3α-yl β 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:

hydrocortisone acetate (50-03-3) → allotetrahydrocortisol 3-glucuronide (30954-21-3)

Guidance literature:

Multi-step reaction with 12 steps

1: 1.5 g / p-toluenesulfonic acid / ethanol; tetrahydrofuran / 4.5 h / Ambient temperature

2: 1.) H₂, 2.) 2 N HCl / 1.) 5percent Pd-C / 1.) ethyl acetate, ethanol, 14 h, atmospheric pressure

3: NaOH / methanol

4: 76 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

5: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C

6: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature

7: 66 percent / 90percent AcOH / 4 h / Ambient temperature

8: 81 percent / pyridine / Ambient temperature

9: 99 percent / 47percent HF / acetonitrile / 0.33 h / Ambient temperature

10: 28 percent / Ag₂CO₃ / toluene / 120 h / Ambient temperature

11: AcONa / methanol / 48 h / Ambient temperature

12: 1.) 2percent methanolic KOH, 2.) pyruvic acid, AcOH / 1.) r.t., 14 h, 2.) CHCl₃, r.t., 14 h

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium hydroxide; hydrogen fluoride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; toluene-4-sulfonic acid; acetic acid; 2-oxo-propionic acid; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1248/cpb.38.1949

Reference yield:

2-((8S,9S,10R,11S,13S,14S,17R)-3-ethoxy-11,17-dihydroxy-10,13-dimethyl-2,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (56736-68-6) → allotetrahydrocortisol 3-glucuronide (30954-21-3)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) H₂, 2.) 2 N HCl / 1.) 5percent Pd-C / 1.) ethyl acetate, ethanol, 14 h, atmospheric pressure

2: NaOH / methanol

3: 76 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

4: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C

5: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature

6: 66 percent / 90percent AcOH / 4 h / Ambient temperature

7: 81 percent / pyridine / Ambient temperature

8: 99 percent / 47percent HF / acetonitrile / 0.33 h / Ambient temperature

9: 28 percent / Ag₂CO₃ / toluene / 120 h / Ambient temperature

10: AcONa / methanol / 48 h / Ambient temperature

11: 1.) 2percent methanolic KOH, 2.) pyruvic acid, AcOH / 1.) r.t., 14 h, 2.) CHCl₃, r.t., 14 h

With pyridine; 1H-imidazole; hydrogenchloride; potassium hydroxide; sodium hydroxide; hydrogen fluoride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; acetic acid; 2-oxo-propionic acid; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1248/cpb.38.1949

Reference yield:

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione (516-41-6,71973-95-0) → allotetrahydrocortisol 3-glucuronide (30954-21-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 76 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 2 h / Ambient temperature

2: 72 percent / K-selectride (potassium tri-sec-butylborohydride) / tetrahydrofuran / 1 h / -78 °C

3: imidazole / dimethylformamide; pyridine / 4 h / Ambient temperature

4: 66 percent / 90percent AcOH / 4 h / Ambient temperature

5: 81 percent / pyridine / Ambient temperature

6: 99 percent / 47percent HF / acetonitrile / 0.33 h / Ambient temperature

7: 28 percent / Ag₂CO₃ / toluene / 120 h / Ambient temperature

8: AcONa / methanol / 48 h / Ambient temperature

9: 1.) 2percent methanolic KOH, 2.) pyruvic acid, AcOH / 1.) r.t., 14 h, 2.) CHCl₃, r.t., 14 h

With pyridine; 1H-imidazole; potassium hydroxide; hydrogen fluoride; sodium acetate; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; acetic acid; 2-oxo-propionic acid; silver carbonate; In tetrahydrofuran; pyridine; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1248/cpb.38.1949

upstream raw materials:

C₃₇H₅₅N₃O₁₅

hydrocortisone acetate

11β,17α,21-trihydroxy-5α-pregnane-3,20-dione

RU 18748

Refernces