(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

Base Information

• Chemical Name: (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene
• CAS No.: 143884-26-8
• Molecular Formula: C₃₅H₆₂O₃Si₂
• Molecular Weight: 587.046
• Mol file: 143884-26-8.mol

Synonyms:(5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

Chemical Property of (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene

There total 6 articles about (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene 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: 96.0%

(5Z,7E,20R)-1α,3β-bis(tert-butyldimethylsilyloxy)-20-cyanomethyl-9,10-seco-5,7,10(19)-pregnatriene (151919-93-6) → (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8)

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at 0 ℃; for 2h;

DOI:10.1021/jm050738x

Reference yield: 88.0%

(R)-3-{(R)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyronitrile → (R)-3-{(R)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-butyraldehyde (131496-31-6,143884-26-8)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -15 - 0 ℃;

DOI:10.1248/cpb.40.1662

Reference yield:

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate (114694-13-2) → (5Z,7E,20R)-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-20-formylmethyl-9,10-seco-5,7,10(19)-pregnatriene (143884-26-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / dimethylsulfoxide / 2 h / 90 °C

2: 96 percent / DIBAL-H / CH₂Cl₂; hexane / 2 h / 0 °C

With diisobutylaluminium hydride; In hexane; dichloromethane; dimethyl sulfoxide;

DOI:10.1021/jm050738x

upstream raw materials:

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

Toluene-4-sulfonic acid (S)-2-{(R)-4-[2-[(3S,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(E)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester

(5Z,7E,20R)-1α,3β-bis(tert-butyldimethylsilyloxy)-20-cyanomethyl-9,10-seco-5,7,10(19)-pregnatriene

(5Z,7E)-(1S,3R,20S)-1,3-bis<(tert-butyldimethylsilyl)oxy>-9,10-seco-22,23-dinor-5,7,10(19)-cholatrienol 22-p-toluenesulfonate

Downstream raw materials:

(5Z,7E,20R,23S)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene

(5Z,7E,20R,23R)-24,24-difluoro-1α,3β-bis<(tert-butyldimethylsilyl)oxy>-23-hydroxy-24-ethoxycarbonyl-9,10-seco-5,7,10(19)-cholatriene

(R)-4-{(1R,3aS,7aR)-4-[2-[(3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohex-(Z)-ylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-pentan-2-ol

C₄₃H₇₁NO₃Si₂