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

Base Information

• Chemical Name: 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
• CAS No.: 1237750-63-8
• Molecular Formula: C₃₈H₆₆O₄Si₂
• Molecular Weight: 643.111
• Mol file: 1237750-63-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 1 articles about 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 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: 70.0%

(3'R,5'R)-3'5'-bis[(tert-butyldimethylsilyl)oxy]-(20S)-20-al-2-methylene-19-nor-pregnacalciferol (845815-90-9) + ethyl diphenylphosphonoacetate (16139-79-0) → 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 (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)

Guidance literature:

ethyl diphenylphosphonoacetate; With sodium hydride; In tetrahydrofuran; mineral oil; at 0 ℃; for 0.166667h; Inert atmosphere;

(3'R,5'R)-3'5'-bis[(tert-butyldimethylsilyl)oxy]-(20S)-20-al-2-methylene-19-nor-pregnacalciferol; In tetrahydrofuran; mineral oil; at -78 - -10 ℃; for 1.5h; Inert atmosphere;

DOI:10.1021/jm100649d

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: 55.0%

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) + ethyllithium (811-49-4) → ethyl (3S)-4-[(1R,3R,7E,17β)-1,3-bis{[tert-butyl(dimethyl)silyl]oxy}-2-methylidene-9,10-secoestra-5,7-dien-17-yl]-3-ethylpentanoate (1237750-65-0)

Guidance literature:

ethyllithium; With dimethylsulfide; copper(I) bromide; In tetrahydrofuran; cyclohexane; benzene; 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; cyclohexane; benzene; at -30 ℃; for 3.5h; diastereoselective reaction; Inert atmosphere;

DOI:10.1021/jm100649d

upstream raw materials:

(3'R,5'R)-3'5'-bis[(tert-butyldimethylsilyl)oxy]-(20S)-20-al-2-methylene-19-nor-pregnacalciferol

ethyl diphenylphosphonoacetate

Downstream 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

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

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