(2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane

Base Information

• Chemical Name: (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane
• CAS No.: 320742-75-4
• Molecular Formula: C₂₄H₃₅N₃OSi
• Molecular Weight: 409.647
• Mol file: 320742-75-4.mol

Synonyms:(2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane

Chemical Property of (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane

There total 7 articles about (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane 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: 87.0%

Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester (320742-74-3) → (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane (320742-75-4)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.tet.2004.06.014

Reference yield: 74.0%

(3S,5S)-6-(tert-butyldiphenylsilyloxy)-3,5-dimethylhexan-1-ol (128329-63-5) → (2S,4S)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane (320742-75-4)

Guidance literature:

With bis(p-nitrophenyl) azidophosphonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 21.5h;

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)-6-azido-2,4-dimethyl-1-(tert-butyldiphenylsilyloxy)hexane (320742-75-4)

Guidance literature:

Multi-step reaction with 5 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

3.1: 9-borabicyclo[3.3.1]nonane dimer / tetrahydrofuran / 0.67 h / sonication

3.2: 71 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -5 °C

4.1: Et₃N; DMAP / CH₂Cl₂ / 0 - 20 °C

5.1: 87 percent / NaN₃ / dimethylformamide / 20 °C

With dmap; lithium aluminium tetrahydride; n-butyllithium; sodium azide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2004.06.014

upstream raw materials:

Methanesulfonic acid (3S,5S)-6-(tert-butyl-diphenyl-silanyloxy)-3,5-dimethyl-hexyl ester

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

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

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

Downstream raw materials:

(+)-kalkitoxin

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

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

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