(R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

Base Information

• Chemical Name: (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide
• CAS No.: 320742-77-6
• Molecular Formula: C₂₉H₄₅NO₂Si
• Molecular Weight: 467.767
• Mol file: 320742-77-6.mol

Synonyms:(R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

Chemical Property of (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide

There total 10 articles about (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide 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: 95.0%

(R)-2-methylbutyric acid (32231-50-8) + (3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexylamine (320742-76-5) → (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide (320742-77-6)

Guidance literature:

With diethyl cyanophosphonate; triethylamine; In dichloromethane; at 20 ℃; for 2.5h; Inert atmosphere;

DOI:10.1021/jo201951s

Reference yield:

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol (128329-63-5) → (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide (320742-77-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 87 percent / NaN₃ / dimethylformamide / 20 °C

3: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

4: 93 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

With dmap; sodium azide; diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.06.014

Reference yield:

(2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane (320742-75-4) → (R)-N-((3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexyl)-2-methylbutanamide (320742-77-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

2: 93 percent / diethyl phosphorocyanidate; Et₃N / dimethylformamide / 0 - 20 °C

With diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.06.014

upstream raw materials:

(R)-2-methylbutyric acid

(3S,5S)-6-(tert-Butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexylamine

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

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

Downstream raw materials:

(2R)-N-methyl-N-[(3S,5S)-dimethyl-6-(tert-butyldiphenylsilyloxy)-hex-1-yl]-2-methylbutyramide

(+)-kalkitoxin

(R)-N,2-dimethyl-N-((3S,5S,6R)-3,5,6-trimethyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)octyl)butanamide

(R)-N-((3S,5S,E)-3,5-dimethyl-8-oxo-8-((R)-2-oxo-4-phenyloxazolidin-3-yl)oct-6-en-1-yl)-N,2-dimethylbutanamide

Refernces

• 1、 Yokokawa, Fumiaki,Asano, Toshinobu,Okino, Tatsufumi,Gerwick, William H.,Shioiri, Takayuki. "An expeditious total synthesis of kalkitoxins: Determination of the absolute stereostructure of natural kalkitoxin". . p. 6859 - 6880. Retrieved 2007/10/03.