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

Base Information

• Chemical Name: (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane
• CAS No.: 946133-92-2
• Molecular Formula: C₂₄H₃₄O₃
• Molecular Weight: 370.532
• Mol file: 946133-92-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about (8S,20R)-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: 70.0%

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester (66774-71-8) + (R)-3-hydroxybutyl-triphenylphosphonium iodide (75419-20-4) → (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane (946133-92-2)

Guidance literature:

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

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester; In tetrahydrofuran; at -20 - 20 ℃; for 21h;

Reference yield: 49.0%

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester (66774-71-8) → (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane (946133-92-2)

Guidance literature:

(R)-3-hydroxybutyl-triphenylphosphonium iodide; With n-butyllithium; In tetrahydrofuran; at -20 ℃; for 1h;

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester; In tetrahydrofuran; at -20 - 20 ℃; for 21h;

Reference yield: 49.0%

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester (66774-71-8) + C22H24OP(1+)*Br(1-) (113730-87-3,85769-75-1) → (8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-hydroxy-pent-(1'E)-en-yl]-pregnane (946133-92-2)

Guidance literature:

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

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester; In tetrahydrofuran; at -20 - 20 ℃; for 22h; diastereoselective reaction;

DOI:10.1016/j.steroids.2014.01.012

upstream raw materials:

Benzoic acid (1R,3aR,4S,7aR)-7a-methyl-1-((S)-1-methyl-2-oxo-ethyl)-octahydro-inden-4-yl ester

(R)-3-hydroxybutyl-triphenylphosphonium iodide

benzoyl chloride

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol

Downstream raw materials:

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

(20R,25R)-1α-[(tert-butyldimethylsilyl)oxy]-2-methylene-25-[(tert-butyldimethyl-silyl)oxy]-19,26-dinor-22-(E)-ene-vitamin D3 tert-butyldimethylsilyl ether

(20R,25R)-2-methylene-19,26-dinor-22-(E)-ene-1α,25-dihydroxyvitamin D3

(8S,20R)-des-A,B-8-benzoyloxy-20-[(4'R)-(tert-butyldimethylsilyl)oxy-pentyl]-pregnane