(5R)-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}-3-ethylnonan-3-ol

Base Information

• Chemical Name: (5R)-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}-3-ethylnonan-3-ol
• CAS No.: 1608457-65-3
• Molecular Formula: C₄₄H₈₂O₃Si₂
• Molecular Weight: 715.304
• Mol file: 1608457-65-3.mol

Synonyms:(5R)-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}-3-ethylnonan-3-ol

Chemical Property of (5R)-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}-3-ethylnonan-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R)-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}-3-ethylnonan-3-ol

There total 2 articles about (5R)-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}-3-ethylnonan-3-ol 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: 86.0%

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) + ethylmagnesium bromide (925-90-6) → (5R)-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}-3-ethylnonan-3-ol (1608457-65-3)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 6h;

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) → (5R)-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}-3-ethylnonan-3-ol (1608457-65-3)

Guidance literature:

Multi-step reaction with 2 steps

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

1.2: 1.5 h / -30 °C

2.1: tetrahydrofuran / 6 h / 20 °C

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; hexane;

DOI:10.1021/jm500392t

Reference yield: 97.0%

(5R)-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}-3-ethylnonan-3-ol (1608457-65-3) → C32H54O3 (1608457-66-4)

Guidance literature:

With camphor-10-sulfonic acid; In methanol; at 0 - 20 ℃; for 1h;

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

ethylmagnesium bromide

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