Tetrahydro-11-deoxycortisol 21-Glucuronide

Base Information

• Chemical Name: Tetrahydro-11-deoxycortisol 21-Glucuronide
• CAS No.: 56162-38-0
• Molecular Formula: C₂₇H₄₂O₁₀
• Molecular Weight: 526.624
• Mol file: 56162-38-0.mol

Synonyms:(3α,5β)-3,17-dihydroxy-20-oxopregnan-21-yl-D-glucopyranosiduronic Acid;3α,17-Dihydroxy-20-oxo-5β-pregnan-21-yl β-D-Glucopyranosiduronic Acid;Tetrahydro-11-deoxy Cortisol 21-O-β-D-Glucuronide;Tetrahydro-11-deoxycortisol 21-Glucuronide

Chemical Property of Tetrahydro-11-deoxycortisol 21-Glucuronide

Chemical Property:

• PSA: 173.98000
• LogP: 0.59900

Purity/Quality:

98% ^*data from raw suppliers

Tetrahydro-11-deoxyCortisol21-O-β-D-Glucuronide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: The 21-monoglucuronide conjugate of Tetrahydro-11-deoxycortisol (T293390).

Technology Process of Tetrahydro-11-deoxycortisol 21-Glucuronide

There total 20 articles about Tetrahydro-11-deoxycortisol 21-Glucuronide 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:

cortexolone 21-acetate (640-87-9) → allotetrahydro-11-deoxycolesterol 21-glucuronide (56162-38-0,103293-13-6,107781-73-7)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂SO₄ / ethanol; dioxane / 1 h / Ambient temperature

2: H₂ / 5percent Pd-C / ethanol; ethyl acetate / 14 h

3: 2N HCl / H₂O

4: NaOH / methanol; dioxane

5: pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

6: 74 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / -78 °C

7: pyridine / 20 h / Ambient temperature

8: 50percent H₂SO₄ / acetone / 0.67 h / Ambient temperature

9: Ag₂CO₃ / toluene / 12 h / Ambient temperature

10: 2percent KOH / methanol / 12 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene;

DOI:10.1248/cpb.33.4281

Reference yield:

3-ethoxy-17α,21-dihydroxy-3,5-pregnadien-20-one 21-acetate (23775-86-2) → allotetrahydro-11-deoxycolesterol 21-glucuronide (56162-38-0,103293-13-6,107781-73-7)

Guidance literature:

Multi-step reaction with 9 steps

1: H₂ / 5percent Pd-C / ethanol; ethyl acetate / 14 h

2: 2N HCl / H₂O

3: NaOH / methanol; dioxane

4: pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

5: 74 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / -78 °C

6: pyridine / 20 h / Ambient temperature

7: 50percent H₂SO₄ / acetone / 0.67 h / Ambient temperature

8: Ag₂CO₃ / toluene / 12 h / Ambient temperature

9: 2percent KOH / methanol / 12 h / Ambient temperature

With pyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sulfuric acid; hydrogen; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; silver carbonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; ethyl acetate; acetone; toluene;

DOI:10.1248/cpb.33.4281

Reference yield:

17α-21-dihydroxy-5-α-pregnane-3,20-dione (312-99-2) → allotetrahydro-11-deoxycolesterol 21-glucuronide (56162-38-0,103293-13-6,107781-73-7)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 3 h / Ambient temperature

2: 74 percent / potassium tri-sec-butylborohydride / tetrahydrofuran / -78 °C

3: pyridine / 20 h / Ambient temperature

4: 50percent H₂SO₄ / acetone / 0.67 h / Ambient temperature

5: Ag₂CO₃ / toluene / 12 h / Ambient temperature

6: 2percent KOH / methanol / 12 h / Ambient temperature

With pyridine; potassium hydroxide; sulfuric acid; pyridinium p-toluenesulfonate; potassium tri-sec-butyl-borohydride; silver carbonate; In tetrahydrofuran; methanol; dichloromethane; acetone; toluene;

DOI:10.1248/cpb.33.4281

upstream raw materials:

methyl (3α-acetoxy-17α-hydroxy-20-oxo-5α-pregnan-21-yl-2',3',4'-tri-O-acetyl-β-D-glucopyranosid)uronate

cortexolone 21-acetate

3-ethoxy-17α,21-dihydroxy-3,5-pregnadien-20-one 21-acetate

17α-21-dihydroxy-5-α-pregnane-3,20-dione

Refernces

• 1、 Hosoda,Yokohama,Ishii,Ito,Nambara. "Preparation of haptens for use in immunoassays of tetrahydro-11-deoxycortisol and its glucuronides.". . p. 4001 - 4007. Retrieved 2007/10/02.