E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester

Base Information

• Chemical Name: E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester
• CAS No.: 141847-50-9
• Molecular Formula: C₂₂H₄₂O₄Si₂
• Molecular Weight: 426.744
• Mol file: 141847-50-9.mol

Synonyms:E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester

Chemical Property of E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester

There total 22 articles about E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester 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: 64.0%

(5R,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-non-8-en-2-ynoic acid methyl ester (161055-42-1) → E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester (141847-50-9)

Guidance literature:

With 1,2-bis-(diphenylphosphino)ethane; Trimethylacetic acid; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In benzene; at 50 ℃; for 22h;

DOI:10.1039/c39940001903

Reference yield:

(1S,2S,4R,6R)-2,4-bis(tert-butyldimethylsilyloxy)-1-methyl-7-oxabicyclo[4.1.0]heptane (121289-20-1) → E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester (141847-50-9)

Guidance literature:

Multi-step reaction with 4 steps

1: H₅IO₆ / diethyl ether

2: Ph₃P, Zn / CH₂Cl₂; pyridine / 1 h / 0 °C

3: 81 percent / LDA / tetrahydrofuran / -78 °C

4: Ph₃P, Et₃N / Pd(OAc)2

With periodic acid; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; palladium diacetate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(97)01005-8

Reference yield:

(1S,2S,4S,6R)-1-Methyl-7-oxa-bicyclo[4.1.0]heptane-2,4-diol (191849-78-2) → E-(3S,5R)-[3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylenecyclohexylidene]acetic acid methyl ester (141847-50-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / imidazole

2: H₅IO₆ / diethyl ether

3: Ph₃P, Zn / CH₂Cl₂; pyridine / 1 h / 0 °C

4: 81 percent / LDA / tetrahydrofuran / -78 °C

5: Ph₃P, Et₃N / Pd(OAc)2

With 1H-imidazole; periodic acid; triethylamine; triphenylphosphine; zinc; lithium diisopropyl amide; palladium diacetate; In tetrahydrofuran; pyridine; diethyl ether; dichloromethane;

DOI:10.1016/S0040-4039(97)01005-8

upstream raw materials:

(5R,7S)-5,7-Bis-(tert-butyl-dimethyl-silanyloxy)-non-8-en-2-ynoic acid methyl ester

methanol

carbon monoxide

Trifluoro-methanesulfonic acid (2S,4R)-2,4-bis-(tert-butyl-dimethyl-silanyloxy)-1-methylene-hept-6-ynyl ester

Downstream raw materials:

[3S-(1E,3α,5β)]-2-[3,5-bis[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-methylenecyclohexylidene]ethanol