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

Base Information

• Chemical Name: 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
• CAS No.: 1237750-56-9
• Molecular Formula: C₄₂H₇₆O₄Si₂
• Molecular Weight: 701.234
• Mol file: 1237750-56-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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: 81.0%

n-butyllithium (109-72-8,29786-93-4) + 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) → 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) + 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 (1237750-64-9)

Guidance literature:

n-butyllithium; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; hexane; at -30 ℃; for 0.25h;

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; With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -30 ℃; for 1.5h;

DOI:10.1021/jm500392t

Reference yield: 74.0%

n-butyllithium (109-72-8,29786-93-4) + ethyl (2Z)-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 (1237750-63-8) → 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) + 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 (1237750-64-9)

Guidance literature:

n-butyllithium; With dimethylsulfide; copper(I) bromide; In tetrahydrofuran; hexane; at -30 ℃; for 0.25h; Inert atmosphere;

ethyl (2Z)-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; With N,N,N,N,N,N-hexamethylphosphoric triamide; chloro-trimethyl-silane; In tetrahydrofuran; hexane; at -30 ℃; for 1.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jm100649d

Reference yield: 95.0%

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) → (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 (1608457-61-9)

Guidance literature:

With diisobutylaluminium hydride; In tetrahydrofuran; toluene; at 0 ℃; for 1.5h;

DOI:10.1021/jm500392t

upstream raw materials:

n-butyllithium

ethyl (2Z)-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

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

Downstream raw materials:

C₃₂H₅₄O₃

(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}heptyl-4-methyl benzenesulfonate

(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

(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