(2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide

Base Information

• Chemical Name: (2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide
• CAS No.: 405297-51-0
• Molecular Formula: C₂₉H₄₆O₃SSi
• Molecular Weight: 502.834
• Mol file: 405297-51-0.mol

Synonyms:(2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide

Chemical Property of (2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide

There total 4 articles about (2S,R_S)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide 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: 92.0%

triisopropylsilyl chloride (13154-24-0) + (2S,RS)-6-benzyloxy-2-hydroxyhexyl p-tolyl sulfoxide (405297-50-9) → (2S,RS)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide (405297-51-0)

Guidance literature:

With 2,6-dimethylpyridine; silver nitrate; In tetrahydrofuran; N,N-dimethyl-formamide; at 20 ℃; for 18h;

DOI:10.1021/ja017177t

Reference yield:

5-benzyloxypentanoic acid methyl ester (31662-20-1) → (2S,RS)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide (405297-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / tetrahydrofuran; hexane; diethyl ether / 2 h / -60 °C

2: 87 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

3: 92 percent / 2,6-lutidine; silver(I) nitrate / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; silver nitrate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja017177t

Reference yield:

lithium (RS)-(+)-methyl p-tolyl sulfoxide (112572-16-4) → (2S,RS)-6-benzyloxy-2-[tris(1-methylethyl)silyl]oxyhexyl p-tolyl sulfoxide (405297-51-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / tetrahydrofuran; hexane; diethyl ether / 2 h / -60 °C

2: 87 percent / DIBAL / CH₂Cl₂; toluene / 1 h / -78 °C

3: 92 percent / 2,6-lutidine; silver(I) nitrate / tetrahydrofuran; dimethylformamide / 18 h / 20 °C

With 2,6-dimethylpyridine; diisobutylaluminium hydride; silver nitrate; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja017177t

upstream raw materials:

triisopropylsilyl chloride

(2S,R_S)-6-benzyloxy-2-hydroxyhexyl p-tolyl sulfoxide

5-benzyloxypentanoic acid methyl ester

lithium (R_S)-(+)-methyl p-tolyl sulfoxide

Downstream raw materials:

phenyl (R)-5-[tris(1-methylethyl)silyl]oxyhexyl sulfone

(2E,4Z,10E,12E)-(7S,9R,17R)-1-[(1,1-dimethylethyl)silyl]oxy-7,9-isopropylidenedioxy-12-(phenylsulfonyl)-17-[tris(1-methylethyl)silyl]oxyoctadeca-2,4,10,12-tetraene

Benzoic acid (R)-2-benzenesulfonyl-1-((E)-2-{(4R,6S)-6-[(2Z,4E)-6-(tert-butyl-dimethyl-silanyloxy)-hexa-2,4-dienyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-vinyl)-6-triisopropylsilanyloxy-heptyl ester