(R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

Base Information

• Chemical Name: (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid
• CAS No.: 1190391-63-9
• Molecular Formula: C₁₉H₂₈O₃Si
• Molecular Weight: 332.515
• Mol file: 1190391-63-9.mol

Synonyms:(R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

Chemical Property of (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid

There total 9 articles about (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid 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: 86.6%

(2R)-2-[(S)-hydroxy(phenyl)methyl]hex-5-ynoic acid (1190391-62-8) + tert-butyldimethylsilyl chloride (18162-48-6) → (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190391-63-9)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 4.16667h; Inert atmosphere;

Reference yield:

hex-5-ynoic acid (53293-00-8) → (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190391-63-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 2.33 h / -25 °C / Inert atmosphere

1.2: 12 h / 20 °C / Cooling; Inert atmosphere

2.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C / Inert atmosphere

2.2: 5 h / 20 °C / Inert atmosphere

3.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere

3.2: 0 - 5 °C

3.3: 0 °C / pH 3

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

With chloro-trimethyl-silane; dihydrogen peroxide; pivaloyl chloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; magnesium chloride; lithium hydroxide; In tetrahydrofuran; water; ethyl acetate; acetonitrile;

Reference yield:

(S)-3-(hex-5-ynoyl)-4-phenyloxazolidin-2-one (1190391-59-3) → (R)-2-((S)-phenyl((trimethylsilyl)oxy)methyl)hex-5-ynoic acid (1190391-63-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: chloro-trimethyl-silane; triethylamine; magnesium chloride / ethyl acetate / 72 h / 20 °C / Inert atmosphere

1.2: 5 h / 20 °C / Inert atmosphere

2.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 3 h / 0 - 5 °C / Inert atmosphere

2.2: 0 - 5 °C

2.3: 0 °C / pH 3

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 4.17 h / 20 °C / Inert atmosphere

With chloro-trimethyl-silane; dihydrogen peroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; magnesium chloride; lithium hydroxide; In tetrahydrofuran; water; ethyl acetate; acetonitrile;

upstream raw materials:

(2R)-2-[(S)-hydroxy(phenyl)methyl]hex-5-ynoic acid

tert-butyldimethylsilyl chloride

hex-5-ynoic acid

(S)-3-(hex-5-ynoyl)-4-phenyloxazolidin-2-one

Downstream raw materials:

4-methoxybenzyl {(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pent-4-yn-1-yl}carbamate

tert-butyl (2S,5R)-2-(4-aminobenzyl)-5-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]pyrrolidine-1-carboxylate

4-methoxybenzyl [(1R)-1-[(R)-{[tert-butyl(dimethyl)silyl]oxy}(phenyl)methyl]-5-(4-nitrophenyl)pent-4-yn-1-yl]carbamate

4-methoxybenzyl ((1R,2R)-1-((tert-butyldimethylsilyl)oxy)-6-(4-nitrophenyl)-5-oxo-1-phenylhexan-2-yl)carbamate