Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)pent-2-enoate

Base Information

• Chemical Name: Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)pent-2-enoate
• CAS No.: 101859-37-4
• Molecular Formula: C₁₈H₃₄O₃Si
• Molecular Weight: 326.552
• Mol file: 101859-37-4.mol

Synonyms:Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)pent-2-enoate;101859-37-4;2-Pentenoic acid, 5-(2-(((1,1-dimethylethyl)dimethylsilyl)oxy)cyclohexyl)-, methyl ester, (1alpha(Z),2beta)-

Chemical Property of Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)pent-2-enoate

Chemical Property:

• Vapor Pressure: 2.24E-05mmHg at 25°C
• Boiling Point: 360.3°Cat760mmHg
• Flash Point: 142.7°C
• Density: 0.94g/cm³
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 8
• Exact Mass: 326.22772148
• Heavy Atom Count: 22
• Complexity: 382

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1CCCCC1CCC=CC(=O)OC
• Isomeric SMILES: CC(C)(C)[Si](C)(C)O[C@H]1CCCC[C@@H]1CC/C=C\C(=O)OC

Technology Process of Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)pent-2-enoate

There total 8 articles about Methyl (Z)-5-((1R,2S)-2-(tert-butyl(dimethyl)silyl)oxycyclohexyl)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: 56.0%

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate (88738-78-7) + 3-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-propionaldehyde (101859-36-3) → (Z)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-pent-2-enoic acid methyl ester (101859-37-4,101976-93-6)

Guidance literature:

With 18-crown-6 ether; KN(Me₄Si)2; In tetrahydrofuran;

DOI:10.1021/jo00362a014

Reference yield:

cyclohexane-1,2-epoxide (286-20-4) → (Z)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-pent-2-enoic acid methyl ester (101859-37-4,101976-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CuI / 1.) Et₂O

2: 75 percent / TEA,DMAP / tetrahydrofuran; dimethylformamide / Heating

3: 1.) O₃, 2.) Me₂S / 1.) MeOH, - 60 deg C

4: 56 percent / KN(Me₄Si)2, 18-C-6 / tetrahydrofuran

With dmap; copper(l) iodide; 18-crown-6 ether; dimethylsulfide; KN(Me₄Si)2; ozone; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo00362a014

Reference yield:

cyclohexane-1,2-epoxide (286-20-4) → (E)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-pent-2-enoic acid methyl ester (101859-37-4,101976-93-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) CuI / 1.) Et₂O

2: 75 percent / TEA,DMAP / tetrahydrofuran; dimethylformamide / Heating

3: 1.) O₃, 2.) Me₂S / 1.) MeOH, - 60 deg C

4: CHCl₃ / Heating

With dmap; copper(l) iodide; dimethylsulfide; ozone; In tetrahydrofuran; chloroform; N,N-dimethyl-formamide;

DOI:10.1021/jo00362a014

upstream raw materials:

bis-(2,2,2-trifluoroethyl)(methoxycarbonylmethyl)phosphonate

3-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-propionaldehyde

cyclohexane-1,2-epoxide

trans-2-but-3-enylcyclohexanol

Downstream raw materials:

tert-Butyl-dimethyl-{(1R,2S)-2-[(E)-5-(tetrahydro-pyran-2-yloxy)-pent-3-enyl]-cyclohexyloxy}-silane

(E)-5-[(1S,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-cyclohexyl]-pent-2-en-1-ol

(1R*,3R*,6S*)-3-((1R*)-2-((2,4-dichlorobenzoyl)oxy)-1-iodoethyl)-2-oxabicyclo<4.4.0>decane

2,4-Dichloro-benzoic acid (Z)-5-[(1S,2R)-2-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pent-2-enyl ester