(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

Base Information

Chemical Name:(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane
CAS No.:1166898-09-4
Molecular Formula:C₂₄H₃₄O₃
Molecular Weight:370.532
Hs Code.:

Synonyms:(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

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Chemical Property of (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

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Technology Process of (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

There total 6 articles about (8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane 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: 61.0%

: 75419-20-4
(R)-3-hydroxybutyl-triphenylphosphonium iodide

: 115527-12-3
(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al

: 1166898-09-4
(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

Guidance literature:: (R)-3-hydroxybutyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -20 ℃;

(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al; In tetrahydrofuran; at -20 - 20 ℃; for 21h;

Reference yield: 48.0%

: 113730-87-3,85769-75-1
C₂₂H₂₄OP⁽¹⁺⁾*Br^(1-)

: 115527-12-3
(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al

: 1166898-09-4
(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

Guidance literature:: C₂₂H₂₄OP⁽¹⁺⁾*Br^(1-); With n-butyllithium; In tetrahydrofuran; at -20 ℃; for 1h;

(20R)-des-A,B-8β-(benzoyloxy)-23,24-dinorcholan-22-al; In tetrahydrofuran; at -20 - 20 ℃; for 22h; diastereoselective reaction;
DOI:10.1016/j.steroids.2014.01.012

Reference yield:

: 98-88-4
benzoyl chloride

: 1166898-09-4
(8S,20S)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane

Guidance literature:: Multi-step reaction with 4 steps

1.1: pyridine / dmap / 24 h / 0 - 4 °C

1.2: 3 h / 20 °C

2.1: triethylamine; pyridine-SO₃ complex / dichloromethane; dimethyl sulfoxide / 1 h / 0 °C / Inert atmosphere

3.1: tetra(n-butyl)ammonium hydroxide / dichloromethane; water / 16 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / tetrahydrofuran / 1 h / -20 °C

4.2: 21 h / -20 - 20 °C

With pyridine; n-butyllithium; pyridine-SO₃ complex; tetra(n-butyl)ammonium hydroxide; triethylamine; dmap; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide;