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

Base Information

• Chemical Name: (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)amino]octadecan-3,4-diol
• CAS No.: 1262283-56-6
• Molecular Formula: C₃₆H₅₉NO₄Si
• Molecular Weight: 597.954

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

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

Chemical Property:

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

There total 2 articles about (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)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:

N-acetyl-D-ribophytosphingosine (21830-28-4) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)amino]octadecan-3,4-diol (1262283-56-6)

Guidance literature:

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

DOI:10.1021/jo101757k

Reference yield:

N,O,O,O-tetraacetyl-D-ribo-phytosphingosine (13018-48-9) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)amino]octadecan-3,4-diol (1262283-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1: methanol; sodium methylate / 0.5 h / 20 °C / Inert atmosphere

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

With methanol; dmap; sodium methylate; triethylamine; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo101757k

Reference yield: 97.0%

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)amino]octadecan-3,4-diol (1262283-56-6) → (2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(acetyl)amino]octadecan-3,4-cyclic Sulfite (1262283-57-7)

Guidance literature:

With thionyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo101757k

upstream raw materials:

N-acetyl-D-ribophytosphingosine

tert-butylchlorodiphenylsilane

N,O,O,O-tetraacetyl-D-ribo-phytosphingosine

Downstream raw materials:

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

(R)-1-((4S,5R)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methyl-4,5-dihydrooxazol-5-yl)pentadecan-1-ol

(4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-2-methyl-6-tetradecyl-5,6-dihydro-4H-1,3-oxazin-5-ol

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