(2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal

Base Information

• Chemical Name: (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal
• CAS No.: 611174-95-9
• Molecular Formula: C₃₀H₃₈O₃Si
• Molecular Weight: 474.715
• Mol file: 611174-95-9.mol

Synonyms:(2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal

Chemical Property of (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal

There total 3 articles about (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal 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: 91.0%

(2S,3S,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentan-1-ol (160488-42-6) → (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal (611174-95-9)

Guidance literature:

(2S,3S,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentan-1-ol; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

With triethylamine; In dichloromethane; at -78 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo8021583

Reference yield: 83.0%

(2R,3R,4S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-2,4-dimethyl-pentan-1-one (611174-86-8) → (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal (611174-95-9)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1055/s-2003-39891

Reference yield:

(3,3-bis-benzyloxy-2-methyl-propoxy)-tert-butyl-diphenyl-silane → (2R,3R,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentanal (611174-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 2 h / -40 °C

1.2: 71 percent / SnCl₄ / CH₂Cl₂

2.1: 83 percent / DIBALH / CH₂Cl₂ / 2 h / -78 °C

With titanium tetrachloride; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1055/s-2003-39891

upstream raw materials:

(2R,3R,4S)-3-Benzyloxy-5-(tert-butyl-diphenyl-silanyloxy)-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-2,4-dimethyl-pentan-1-one

(2S,3S,4S)-3-(benzyloxy)-5-(tert-butyldiphenylsilyloxy)-2,4-dimethylpentan-1-ol