(2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one

Base Information

• Chemical Name: (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one
• CAS No.: 872356-73-5
• Molecular Formula: C₃₉H₆₃NO₄Si
• Molecular Weight: 638.019
• Mol file: 872356-73-5.mol

Synonyms:(2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one

Chemical Property of (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one

There total 3 articles about (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one 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: 88.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one (437609-37-5) → (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one (872356-73-5)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide;

DOI:10.1021/jo051147h

Reference yield:

(S)-N-(tert-butoxycarbonyl)serine (3262-72-4) → (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one (872356-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / N-methylmorpholine; 1-(3-methylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1 h / -15 °C

2: 70 percent / s-BuMgCl / tetrahydrofuran; diethyl ether / -15 - 20 °C

3: 88 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide

With 4-methyl-morpholine; 1H-imidazole; dmap; 1-ethyl-3-(3-methylaminopropyl)-carbodiimide hydrochloride; s-butylmagnesium chloride; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo051147h

Reference yield:

N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide (122709-20-0) → (2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldiphenylsilanyloxyoctadecan-3-one (872356-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / s-BuMgCl / tetrahydrofuran; diethyl ether / -15 - 20 °C

2: 88 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide

With 1H-imidazole; dmap; s-butylmagnesium chloride; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jo051147h

upstream raw materials:

tert-butylchlorodiphenylsilane

(2S)-2-(N-tert-butoxycarbonyl)amino-1-hydroxyoctadecan-3-one

(S)-N-(tert-butoxycarbonyl)serine

N-(tert-butoxycarbonyl)-L-serine N'-methoxy-N'-methylamide

Downstream raw materials:

(2S,3R)-3-benzyloxy-2-(N-hexacosanoylamino)-1-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)octadecane

(2S,3R)-3-O-benzyl-2-(N-hexacosanoylamino)octadecan-1,3-diol

(2S,3R)-2-(N-tert-butyloxycarbonyl)amino-1-tert-butyldiphenylsilanyloxy-3-benzyloxyoctadecane

(2S,3R)-2-amino-3-benzyloxyoctadecan-1-ol