(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

Base Information

Chemical Name:(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane
CAS No.:872356-71-3
Molecular Formula:C₃₆H₆₇NO₄Si
Molecular Weight:606.018
Hs Code.:

Synonyms:(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

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Chemical Property of (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

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Technology Process of (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

There total 6 articles about (2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane 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: 53.0%

: 872356-70-2
(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-ol

: 100-39-0
benzyl bromide

: 872356-71-3
(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

Guidance literature:: With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃;
DOI:10.1021/jo051147h

Reference yield:

: 872356-69-9
(2S)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxyoctadecan-3-one

: 872356-71-3
(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / LiAl(t-BuO)3H / ethanol / 6 h / -78 °C

2: 53 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 0 - 20 °C

With tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; In ethanol; N,N-dimethyl-formamide;
DOI:10.1021/jo051147h

Reference yield:

: 3262-72-4
(S)-N-(tert-butoxycarbonyl)serine

: 872356-71-3
(2S,3R)-2-(N-tert-butoxycarbonyl)amino-1-tert-butyldimethylsilanyloxy-3-benzyloxyoctadecane

Guidance literature:: Multi-step reaction with 5 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: 83 percent / imidazole; 4-dimethylaminopyridine / dimethylformamide

4: 86 percent / LiAl(t-BuO)3H / ethanol / 6 h / -78 °C

5: 53 percent / NaH; tetrabutylammonium iodide / dimethylformamide / 0 - 20 °C

With 4-methyl-morpholine; 1H-imidazole; dmap; 1-ethyl-3-(3-methylaminopropyl)-carbodiimide hydrochloride; s-butylmagnesium chloride; tetra-(n-butyl)ammonium iodide; sodium hydride; lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo051147h