(20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate

Base Information

• Chemical Name: (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate
• CAS No.: 161579-69-7
• Molecular Formula: C₂₈H₃₇BrO₄
• Molecular Weight: 517.503
• Mol file: 161579-69-7.mol

Synonyms:(20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate

Chemical Property of (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate

There total 1 articles about (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate 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-benzoyloxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one (74214-19-0) → (20S)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate + (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate (161579-69-7)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; at 5 ℃; for 0.5h;

DOI:10.1016/0039-128X(94)90101-5

Reference yield: 72.0%

formic acid (64-18-6) + (20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate (161579-69-7) → (20R)-5-bromo-6β,19-epoxy-5α-pregnane-3β,20-diyl 3-benzoate 20-formate (161579-71-1)

Guidance literature:

With toluene-4-sulfonic acid; at 30 ℃; for 18h;

DOI:10.1016/0039-128X(94)90101-5

Reference yield:

(20R)-5-bromo-6β,19-epoxy-20-hydroxy-5α-pregnan-3β-yl benzoate (161579-69-7) → (20R)-3β,20-dihydroxypregn-5-en-19-al 3-benzoate 20-formate (161579-73-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / TsOH*H₂O / 18 h / 30 °C

2: 82 percent / Zn / 2-methyl-propan-2-ol; H₂O / 1 h / Heating

3: 86 percent / Jones reagent / acetone / 0.08 h / 5 °C

With jones reagent; toluene-4-sulfonic acid; zinc; In water; acetone; tert-butyl alcohol;

DOI:10.1016/0039-128X(94)90101-5

upstream raw materials:

3β-benzoyloxy-5-bromo-6β,19-epoxy-5α-pregnan-20-one

Downstream raw materials:

(20R)-5-bromo-6β,19-epoxy-5α-pregnane-3β,20-diyl 3-benzoate 20-formate

(20R)-19-hydroxypregn-5-ene-3β,20-diyl 3-benzoate 20-formate

(20R)-3β,20-dihydroxypregn-5-en-19-al 3-benzoate 20-formate

(19E)-3β-hydroxy-20-oxopregn-5-en-19-al 3-benzoate 19-(O-carboxymethyl)oxime methylester