(2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

Base Information

• Chemical Name: (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene
• CAS No.: 320742-72-1
• Molecular Formula: C₂₄H₃₄OSi
• Molecular Weight: 366.619
• Mol file: 320742-72-1.mol

Synonyms:(2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

Chemical Property of (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene

There total 9 articles about (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene 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: 63.0%

Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester (321162-62-3) → (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene (320742-72-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; for 1.5h; Heating;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol (198124-61-7) → (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene (320742-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 - 20 °C

2.1: 63 percent / LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; hexane;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

(2S,4S)-5-((tert-butyldiphenylsilyl)oxy)-2,4-dimethylpentan-1-ol (638188-59-7) → (2S,4S)-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)-5-hexene (320742-72-1)

Guidance literature:

Multi-step reaction with 2 steps

1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: n-BuLi / 0 °C

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; 1: Swern oxidation;

DOI:10.1021/ol035846x

upstream raw materials:

Toluene-4-sulfonic acid (1R,2R)-1-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-2-methyl-but-3-enyl ester

Methyltriphenylphosphonium bromide

(3R,4R,5R)-3,5-dimethyl-6-[tert-butyldiphenylsilyloxy]-hex-1-en-4-ol

(R)-3-[(tert-butyldiphenylsilyl)oxy]-2-methylpropanal

Downstream raw materials:

C₂₄H₃₆O₃Si

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol