(S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

Base Information

• Chemical Name: (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal
• CAS No.: 142777-78-4
• Molecular Formula: C₃₃H₆₀O₃Si₂
• Molecular Weight: 561.009
• Mol file: 142777-78-4.mol

Synonyms:(S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

Chemical Property of (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal

There total 13 articles about (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal 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: 89.0%

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane) (957214-02-7) → (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal (142777-78-4,1257126-71-8)

Guidance literature:

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane); With trifluoroacetic acid; In chloroform; water; at 0 ℃; for 0.416667h;

With sodium hydrogencarbonate; In chloroform; water;

Reference yield:

(8S,20S)-de-A,B-20-(hydroxymethyl)pregnan-8-ol (64190-52-9) → (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal (142777-78-4,1257126-71-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 87 percent / pyridine / -20 - 0 °C

2: 88 percent / pyridinium chlorochromate (PCC) / CH₂Cl₂ / 1 h / Ambient temperature

3: n-BuLi / tetrahydrofuran / -78 °C

4: 88 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 25 min, 2) RT, 20 min

5: 1) (COCl)2, 2) Et₃N / 1) DMSO, CH₂Cl₂, -60 deg C, 30 min.

With pyridine; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; triethylamine; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)79565-7

Reference yield:

Acetic acid (S)-2-{(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-7a-methyl-octahydro-inden-1-yl}-propyl ester (141404-12-8) → (S)-2-((1R,3aS,7aR,E)-4-(2-((3R,5R)-3,5-bis(tertbutyldimethylsilyloxy)cyclohexylidene)ethylidene)-7a-methyloctahydro-1H-inden-1-yl)propanal (142777-78-4,1257126-71-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / LiAlH₄ / tetrahydrofuran / 1) 0 deg C, 25 min, 2) RT, 20 min

2: 1) (COCl)2, 2) Et₃N / 1) DMSO, CH₂Cl₂, -60 deg C, 30 min.

With lithium aluminium tetrahydride; oxalyl dichloride; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)79565-7

upstream raw materials:

(E)-(1R,3R,20S)-1,3-Bis-(tert-butyl-dimethyl-silanyloxy)-20-methyl-19-nor-9,10-seco-pregna-5,7-dien-21-ol

((1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((S)-1,1-dimethoxypropan-2-yl)-7a-methyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diyl)bis(oxy)bis(tertbutyldimethylsilane)

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

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

Downstream raw materials:

ethyl (2E,4R)-4-((1R,3R,7E,17β)-1,3-bis[tert-butyl-(dimethyl)silyloxy]-9,10-secoestra-5,7-dien-17-yl)-2-methylpent-2-enoate

(1R,3R)-5-((E)-2-((1R,3aS,7aR)-1-((2R,5S,Z)-6-hydroxy-5,6-dimethylhept-3-en-2-yl)-7amethyldihydro-1H-inden-4(2H,5H,6H,7H,7aH)-ylidene)ethylidene)cyclohexane-1,3-diol

(1R,3aS,7aR)-4-[2-[(3R,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-cyclohexylidene]-eth-(E)-ylidene]-1-((E)-(R)-7-ethyl-1-methyl-7-triethylsilanyloxy-non-2-enyl)-7a-methyl-octahydro-indene

Δ²²,22E,19-nor-24,24-dihomo-26,27-dihomo-1α,25-dihydroxyvitamin D3