(+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate

Base Information

• Chemical Name: (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate
• CAS No.: 173657-00-6
• Molecular Formula: C₁₇H₂₆O₂Si
• Molecular Weight: 290.478
• Mol file: 173657-00-6.mol

Synonyms:(+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate

Chemical Property of (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate

There total 6 articles about (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-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: 99.0%

(+)-methyl (R)-E-3-(phenyldimethylsilyl)hept-4-enoate (142730-71-0) + methyl iodide (74-88-4) → (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate (173657-00-6)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide; In tetrahydrofuran; hexane; -78 deg C, 20 min; 20 min; to 0 deg C;

DOI:10.1016/0040-4020(95)00736-R

Reference yield:

pent-1-yn-3-ol (4187-86-4) → (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate (173657-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾ / tetrahydrofuran / 18 h / Heating

2: 1.) titanium tetraisopropoxide, L-(+)-diethyl tartrate, 4 A molecular sieves, 2.) 5.48 M tert-butylhydroperoxide, 3.) dimethyl sulphide / 1.) CH₂Cl₂, 20 min, 2.) CH₂Cl₂, -20 deg C, 48 h, 3.) CH₂Cl₂, 1 h

3: 93 percent / propionic acid / toluene / 30 min, reflux, addition repeated 3 times

4: 99 percent / LDA, HMPA / tetrahydrofuran; hexane / -78 deg C, 20 min; 20 min; to 0 deg C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethylsulfide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; propionic acid; lithium diisopropyl amide; bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/0040-4020(95)00736-R

Reference yield:

Dimethylphenylsilane (766-77-8) → (+)-methyl (2R,3S)-E-2-methyl-3-(phenyldimethylsilyl)hept-4-enoate (173657-00-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾ / tetrahydrofuran / 18 h / Heating

2: 1.) titanium tetraisopropoxide, L-(+)-diethyl tartrate, 4 A molecular sieves, 2.) 5.48 M tert-butylhydroperoxide, 3.) dimethyl sulphide / 1.) CH₂Cl₂, 20 min, 2.) CH₂Cl₂, -20 deg C, 48 h, 3.) CH₂Cl₂, 1 h

3: 93 percent / propionic acid / toluene / 30 min, reflux, addition repeated 3 times

4: 99 percent / LDA, HMPA / tetrahydrofuran; hexane / -78 deg C, 20 min; 20 min; to 0 deg C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; N,N,N,N,N,N-hexamethylphosphoric triamide; dimethylsulfide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; propionic acid; lithium diisopropyl amide; bis(2,5-norbornene)tris(tert-butyl)phosphine-platinum⁽⁰⁾; In tetrahydrofuran; hexane; toluene;

DOI:10.1016/0040-4020(95)00736-R

upstream raw materials:

Trimethyl orthoacetate

(R)-(E)-(-)-1-(Dimethylphenylsilyl)-1-penten-3-ol

methyl iodide

(+)-methyl (R)-E-3-(phenyldimethylsilyl)hept-4-enoate

Downstream raw materials:

(+)-(3R,4S,5R)-5-((1'S)-hydroxypropyl)-3-methyl-4-(phenyldimethylsilyl)-dihydrofuran-2-one

(-)-(3R,4S,5S)-5-((1'R)-hydroxypropyl)-3-methyl-4-(phenyldimethylsilyl)-dihydrofuran-2-one