(4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one

Base Information

• Chemical Name: (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one
• CAS No.: 1262283-55-5
• Molecular Formula: C₃₅H₅₅NO₄Si
• Molecular Weight: 581.912
• Mol file: 1262283-55-5.mol

Synonyms:(4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one

Chemical Property of (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one

There total 5 articles about (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-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: 76.0%

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-diol (1224436-76-3) → (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one (1262283-55-5)

Guidance literature:

With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -30 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jo101757k

Reference yield: 53.0%

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-cyclic sulfate (1262283-52-2) → (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one (1262283-55-5) + (4S,5R)-4-((tert-butyldiphenylsilyloxy)methyl)-5-((R)-1-hydroxypentadecyl)oxazolidin-2-one (1262283-54-4)

Guidance literature:

(2S,3S,4R)-1-(tert-butyldiphenylsilyloxy)-2-[N-(tert-butyloxycarbonyl)amino]octadecan-3,4-cyclic sulfate; In acetonitrile; at 45 ℃; for 2h; Inert atmosphere;

With sulfuric acid; water; In tetrahydrofuran; acetonitrile; at 20 ℃; for 1h; regioselective reaction; Inert atmosphere;

DOI:10.1021/jo101757k

Reference yield:

D-ribo-phytosphingosine (554-62-1) → (4S,5S,6S)-4-((tert-butyldiphenylsilyloxy)methyl)-5-hydroxy-6-tetradecyl-1,3-oxazinan-2-one (1262283-55-5)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3.1: thionyl chloride; triethylamine / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: sodium periodate; ruthenium(III) chloride trihydrate / tetrachloromethane; water; acetonitrile / 2 h / 20 °C / Inert atmosphere

5.1: acetonitrile / 2 h / 45 °C / Inert atmosphere

5.2: 1 h / 20 °C / Inert atmosphere

With dmap; sodium periodate; thionyl chloride; ruthenium(III) chloride trihydrate; triethylamine; sodium hydroxide; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo101757k

upstream raw materials:

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

C₃₉H₆₃NO₆SSi

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

D-ribo-phytosphingosine