(5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester

Base Information

• Chemical Name: (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester
• CAS No.: 114694-16-5
• Molecular Formula: C₂₅H₃₆O₅
• Molecular Weight: 416.558

Synonyms:(5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester

Chemical Property of (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester

There total 9 articles about (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10⁽¹⁹⁾-pregnatriene-20-carboxylic acid methyl ester 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:

(5Z,7E)-(3S,20S)-3-hydroxy-9,10-seco-5,7,10(19)pregnatriene-20-carboxylic acid methyl ester (97903-24-7) → (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10(19)-pregnatriene-20-carboxylic acid methyl ester (114694-16-5)

Guidance literature:

With tert.-butylhydroperoxide; selenium(IV) oxide; Yield given. Multistep reaction;

DOI:10.1016/S0040-4039(00)61826-9

Reference yield:

3β-hydroxy-22,23-dinor-5,7-choladienic acid methyl ester (99518-39-5) → (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10(19)-pregnatriene-20-carboxylic acid methyl ester (114694-16-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) benzene, ethyl ether, irradiation, 40 min, 2.) ethanol, reflux, 3 h

2: pyridine / 20 h / 4 °C

3: potassium bicarbonate / CH₂Cl₂ / 24 h / 55 °C

4: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 6 mg / 0.25 h / 55 °C

With pyridine; tert.-butylhydroperoxide; selenium(IV) oxide; potassium hydrogencarbonate; In dichloromethane;

DOI:10.1021/jo00250a009

Reference yield:

(3β,20S)-3-<(tert-butyldimethylsilyl)oxy>pregn-5-ene-20-carboxylic acidmethyl ester (69454-87-1) → (5Z,7E)-(1S,3R,20S)-1-hydroxy-3-acetoxy-9,10-seco-5,7,10(19)-pregnatriene-20-carboxylic acid methyl ester (114694-16-5)

Guidance literature:

Multi-step reaction with 6 steps

2: 1.) benzene, ethyl ether, irradiation, 40 min, 2.) ethanol, reflux, 3 h

3: pyridine / 20 h / 4 °C

4: potassium bicarbonate / CH₂Cl₂ / 24 h / 55 °C

5: 12.5 mg / 3.0 M tert-butyl hydroperoxide in toluene, selenium dioxide, pyridine / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 6 mg / 0.25 h / 55 °C

With pyridine; tert.-butylhydroperoxide; selenium(IV) oxide; potassium hydrogencarbonate; In dichloromethane;

DOI:10.1021/jo00250a009

upstream raw materials:

acetic acid

(S)-2-{(1R,3aS,7aR)-4-[(R)-2-((1R,3S,5R)-3-Hydroxy-2-methylene-bicyclo[3.1.0]hex-1-yl)-2-methoxy-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propionic acid methyl ester

(5Z,7E)-(3S,20S)-3-hydroxy-9,10-seco-5,7,10⁽¹⁹⁾pregnatriene-20-carboxylic acid methyl ester

hydroxybisnorcholenic acid

Downstream raw materials:

1-alpha-hydroxybishomopregnacholecalciferol-22 aldehyde

23,24,25,26,27-pentanor-1,22-(OH)2D₃

(S)-2-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Dihydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propionic acid methyl ester

(S)-2-{(1R,7aR)-4-[2-[(S)-5-Hydroxy-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propionaldehyde

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