(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol
• CAS No.: 1224436-76-3
• Molecular Formula: C₃₉H₆₅NO₅Si
• Molecular Weight: 656.034
• Mol file: 1224436-76-3.mol

Synonyms:(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol

Chemical Property of (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol

There total 4 articles about (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol 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: 98.0%

tert-butylchlorodiphenylsilane (58479-61-1) + tert-butyl [(2S,3S,4R)-1,3,4-trihydroxyoctadecan-2-yl]carbamate (175696-50-1) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol (1224436-76-3)

Guidance literature:

With dmap; triethylamine; In dichloromethane; N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo101757k

Reference yield: 72.0%

di-tert-butyl dicarbonate (24424-99-5) + (2S,3S,4R)-2-amino-1-((tert-butyldiphenylsilyl)oxy)octadecane-3,4-diol (1224436-75-2) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol (1224436-76-3)

Guidance literature:

With triethylamine; In acetonitrile;

DOI:10.1021/bc9005255

Reference yield:

D-ribo-phytosphingosine (554-62-1) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol (1224436-76-3)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / ethanol; water / 0 - 20 °C / Inert atmosphere

2: dmap; triethylamine / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With dmap; triethylamine; sodium hydroxide; In ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo101757k

upstream raw materials:

di-tert-butyl dicarbonate

(2S,3S,4R)-2-amino-1-((tert-butyldiphenylsilyl)oxy)octadecane-3,4-diol

D-ribo-phytosphingosine

tert-butylchlorodiphenylsilane

Downstream raw materials:

C₅₃H₇₃NO₇Si

C₃₉H₆₃NO₆SSi

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-cyclic sulfate

(4S,5R)-4-((tert-butyldiphenylsilyloxy)methyl)-5-((R)-1-hydroxypentadecyl)oxazolidin-2-one