(4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal

Base Information

• Chemical Name: (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal
• CAS No.: 360787-69-5
• Molecular Formula: C₁₉H₃₂O₅SSi
• Molecular Weight: 400.612
• Mol file: 360787-69-5.mol

Synonyms:(4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal

Chemical Property of (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal

There total 7 articles about (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal 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: 98.0%

(S)-5-methyl-5-tert-butyldimethylsilyloxy-6-tosyloxyhexene (360788-05-2) → (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal (360787-69-5)

Guidance literature:

(S)-5-methyl-5-tert-butyldimethylsilyloxy-6-tosyloxyhexene; With ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at 25 ℃; for 8h; Further stages.;

DOI:10.1021/jo000249z

Reference yield:

(S)-(-)-2-methyl-5-hexene-1,2-diol (143192-18-1) → (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal (360787-69-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 88 percent / Et₃N; DMAP / CH₂Cl₂ / 20 °C

2: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

3: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; ozone; triethylamine; In dichloromethane;

DOI:10.1039/b209990j

Reference yield:

(S)-2-hydroxy-2-methylhex-5-enyl 4-methylbenzenesulfonate (360788-04-1) → (4S)-4-methyl-5-(p-tolylsulfonyloxy)-4-(tert-butyldimethylsilyloxy)pentanal (360787-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / Et₃N; DMAP / CH₂Cl₂ / 15 h / 20 °C

2: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

With dmap; ozone; triethylamine; In dichloromethane;

DOI:10.1039/b209990j

upstream raw materials:

(S)-5-methyl-5-tert-butyldimethylsilyloxy-6-tosyloxyhexene

t-butyldimethylsiyl triflate

(S)-(-)-2-methyl-5-hexene-1,2-diol

p-toluenesulfonyl chloride

Downstream raw materials:

methyl 3-benzyl-2,3,3a,4,5,7-hexahydro-4-[2-(S)-(tert-butyldimethylsilyloxy)-2-(tosyloxymethyl)propyl]-1H-pyrrolo(2,3-d)carbazole-6-carboxylate