(2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

Base Information

• Chemical Name: (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde
• CAS No.: 343969-42-6
• Molecular Formula: C₂₁H₄₀O₃Si₂
• Molecular Weight: 396.718
• Mol file: 343969-42-6.mol

Synonyms:(2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

Chemical Property of (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde

There total 10 articles about (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde 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: 90.0%

(Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol (338956-81-3) → (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde (343969-42-6)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 0.25h;

Reference yield:

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol (84985-78-4) → (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde (343969-42-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 39 percent / di-isopropyl azodicarboxylate; triphenylphosphine / toluene / 0.5 h / 20 °C

2.1: 20 percent / selenium dioxide / CH₂Cl₂; acetonitrile / 18 h / Heating

3.1: 88 percent / imidazole / dimethylformamide / 18 h / 20 °C

4.1: 96 percent / Cu(OAc)2*H₂O / methanol; CHCl₃ / 18 h / 20 °C

5.1: 88 percent / imidazole / dimethylformamide / 18 h / 20 °C

6.1: Pb(OAc)4; pyridine / CH₂Cl₂ / 1.5 h / 0 °C

6.2: 63 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1.5 h / 0 °C

7.1: 90 percent / Dess-Martin reagent / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-imidazole; lead(IV) acetate; selenium(IV) oxide; copper diacetate; di-isopropyl azodicarboxylate; Dess-Martin periodane; triphenylphosphine; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Mitsunobu reaction / 7.1: Dess-Martin oxidation;

Reference yield:

Pyridine-2-carboxylic acid (1S,3R)-3-(tert-butyl-dimethyl-silanyloxy)-5-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester (343969-45-9) → (2Z)-[(3R,5S)-3,5-di-(tert-butyldimethylsilyloxy)-2-methylenecyclohexylidene]acetaldehyde (343969-42-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 96 percent / Cu(OAc)2*H₂O / methanol; CHCl₃ / 18 h / 20 °C

2.1: 88 percent / imidazole / dimethylformamide / 18 h / 20 °C

3.1: Pb(OAc)4; pyridine / CH₂Cl₂ / 1.5 h / 0 °C

3.2: 63 percent / NaBH₄; CeCl₃*7H₂O / methanol / 1.5 h / 0 °C

4.1: 90 percent / Dess-Martin reagent / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 1H-imidazole; lead(IV) acetate; copper diacetate; Dess-Martin periodane; In methanol; dichloromethane; chloroform; N,N-dimethyl-formamide; 4.1: Dess-Martin oxidation;

upstream raw materials:

(Z,3R,5S)-[3,5-bis(tert-butyldimethylsilyl)oxy-2-methylenecyclohexylidene]ethanol

tert-butyldimethylsilyl chloride

(4R,7aR)-1-((2R,5R,E)-5,6-dimethylhept-3-en-2-yl)-4-((R,Z)-1-hydroxy-2-((S)-5-hydroxy-2-methylenecyclohexylidene)ethyl)-7a-methyloctahydro-1H-inden-4-ol

Pyridine-2-carboxylic acid (R)-3-[(R)-2-hydroxy-2-[(1R,3aR,4R,7aR)-4-hydroxy-7a-methyl-1-((E)-(1R,4R)-1,4,5-trimethyl-hex-2-enyl)-octahydro-inden-4-yl]-eth-(Z)-ylidene]-4-methylene-cyclohexyl ester