(4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal

Base Information

• Chemical Name: (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal
• CAS No.: 1608457-69-7
• Molecular Formula: C₄₁H₇₄O₃Si₂
• Molecular Weight: 671.208
• Mol file: 1608457-69-7.mol

Synonyms:(4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal

Chemical Property of (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal

There total 4 articles about (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal 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: 62.0%

(4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanenitrile (1608457-68-6) → (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal (1608457-69-7)

Guidance literature:

With tetrahydrofuran; diisobutylaluminium hydride; In tetrahydrofuran; toluene; at -20 - 0 ℃; for 3h;

DOI:10.1021/jm500392t

Reference yield:

ethyl (3S)-3-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}heptanoate (1237750-56-9) → (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal (1608457-69-7)

Guidance literature:

Multi-step reaction with 4 steps

1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / 0 °C

2: pyridine / 15 h / 0 °C

3: dimethyl sulfoxide / 1 h / 70 °C

4: diisobutylaluminium hydride; tetrahydrofuran / tetrahydrofuran; toluene / 3 h / -20 - 0 °C

With tetrahydrofuran; pyridine; diisobutylaluminium hydride; In tetrahydrofuran; dimethyl sulfoxide; toluene;

DOI:10.1021/jm500392t

Reference yield:

ethyl (2E)-4-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]pent-2-enoate (1237750-59-2) → (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanal (1608457-69-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(I) bromide dimethylsulfide complex / hexane; tetrahydrofuran / 0.25 h / -30 °C

1.2: 1.5 h / -30 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / 0 °C

3.1: pyridine / 15 h / 0 °C

4.1: dimethyl sulfoxide / 1 h / 70 °C

5.1: diisobutylaluminium hydride; tetrahydrofuran / tetrahydrofuran; toluene / 3 h / -20 - 0 °C

With tetrahydrofuran; pyridine; copper(I) bromide dimethylsulfide complex; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dimethyl sulfoxide; toluene;

DOI:10.1021/jm500392t

upstream raw materials:

ethyl (3S)-3-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}heptanoate

(4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanenitrile

ethyl (2E)-4-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]pent-2-enoate

(3R)-3-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}heptan-1-ol

Downstream raw materials:

(4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octan-1-ol

(5R)-5-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}-2-methylnonan-2-ol

methyl (4R)-4-{1-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]ethyl}octanoate