(2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol

Base Information

• Chemical Name: (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol
• CAS No.: 103931-03-9
• Molecular Formula: C₅₂H₈₉NO₃Si
• Molecular Weight: 804.369
• Mol file: 103931-03-9.mol

Synonyms:(2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol

Chemical Property of (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol

There total 7 articles about (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-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:

Octadecanoic acid {(E)-(1S,2R)-2-(tert-butyl-diphenyl-silanyloxy)-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-amide → (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol (103931-03-9)

Guidance literature:

With boron trifluoride diethyl etherate; thiophenol; In dichloromethane; at 0 ℃;

DOI:10.1080/07328300600803518

Reference yield:

stearic acid (57-11-4) → (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol (103931-03-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 80 percent / 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline / ethanol / 50 °C

2: Et₃N / CH₂Cl₂

3: imidazole / CH₂Cl₂

4: PhSH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With 1H-imidazole; boron trifluoride diethyl etherate; thiophenol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In ethanol; dichloromethane;

DOI:10.1080/07328300600803518

Reference yield:

Octadecanoic acid {(E)-(1S,2R)-2-hydroxy-1-[(4-methoxy-phenyl)-diphenyl-methoxymethyl]-heptadec-3-enyl}-amide → (2S,3R,4E)-3-O-tert-butyldiphenylsilyl-2-octadecanamido-octadec-4-ene-1,3-diol (103931-03-9)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / CH₂Cl₂

2: PhSH; BF₃*OEt₂ / CH₂Cl₂ / 0 °C

With 1H-imidazole; boron trifluoride diethyl etherate; thiophenol; In dichloromethane;

DOI:10.1080/07328300600803518

upstream raw materials:

4-nitrophenyl stearate

erythro-4-(1-hydroxy-2-hexadecenyl)-2-phenyl-Δ²-oxazoline

tert-butylchlorodiphenylsilane

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol

Downstream raw materials:

Diisopropyl-phosphoramidous acid (E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyl ester methyl ester

(2S,3R,4E)-2-(N-stearoylamino)-4-octadecene-1,3-diol

C₅₇H₁₀₁N₂O₅PSSi

Toluene-4-sulfonate(2-{[(E)-(2S,3R)-3-(tert-butyl-diphenyl-silanyloxy)-2-octadecanoylamino-octadec-4-enyloxy]-methoxy-phosphanyloxy}-ethyl)-trimethyl-ammonium;