(2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid

Base Information

• Chemical Name: (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid
• CAS No.: 79568-69-7
• Molecular Formula: C₂₂H₃₀O₄Si
• Molecular Weight: 386.563
• Mol file: 79568-69-7.mol

Synonyms:(2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid

Chemical Property of (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid

There total 6 articles about (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic 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: 87.0%

trimethylaluminum (75-24-1) + (2S,3S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carboxylic acid (79568-68-6) → (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid (79568-69-7)

Guidance literature:

In Petroleum ether; at 25 ℃; for 40h;

DOI:10.1021/jo00338a046

Reference yield:

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol (88159-03-9) → (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid (79568-69-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Lindlar / methanol

2: 87 percent / t-BuOOH, d-diethyl tartrate, Ti(O-i-Pr)4 / CH₂Cl₂ / -20 °C

3: 79 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O

4: 87 percent / petroleum ether / 40 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; Diethyl tartrate; hydrogen; ruthenium trichloride; Lindlar's catalyst; In methanol; tetrachloromethane; dichloromethane; water; acetonitrile; Petroleum ether;

DOI:10.1021/jo00338a046

Reference yield:

(Z)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol (79568-67-5) → (2S,3R)-5-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-3-methyl-pentanoic acid (79568-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / t-BuOOH, d-diethyl tartrate, Ti(O-i-Pr)4 / CH₂Cl₂ / -20 °C

2: 79 percent / NaIO₄ / RuCl₃ / CCl₄; acetonitrile; H₂O

3: 87 percent / petroleum ether / 40 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium periodate; Diethyl tartrate; ruthenium trichloride; In tetrachloromethane; dichloromethane; water; acetonitrile; Petroleum ether;

DOI:10.1021/jo00338a046

upstream raw materials:

trimethylaluminum

(2S,3S)-3-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-oxirane-2-carboxylic acid

5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-yn-1-ol

(Z)-5-(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)pent-2-en-1-ol

Downstream raw materials:

(2S,3R)-2-Acetoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentanoic acid

C₃₉H₅₂O₈Si

C₅₀H₆₈O₁₁Si₂