Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

Base Information

• Chemical Name: Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester
• CAS No.: 176776-97-9
• Molecular Formula: C₆₆H₁₁₃ClN₃O₁₃P
• Molecular Weight: 1223.06
• Mol file: 176776-97-9.mol

Synonyms:

Chemical Property of Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester

There total 4 articles about Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester 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: 42.0%

(2-Chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate (148286-68-4) + N4-Palmitoyl-1-β-D-arabinofuranosylcytosin (55726-45-9) → Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester (176776-97-9)

Guidance literature:

With pyridine; 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; for 2.66667h;

Reference yield:

1,2-di-O-palmitoyl-3-O-benzyl-rac-glycerol (69176-47-2) → Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester (176776-97-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 72 percent / H₂ / Pd/C / hexane

2: 69 percent / Et₃N / CHCl₃ / 1.) ice bath, 20 min, 2.) r.t., 3,5 h

3: 42 percent / pyridine, 2,4,6-triisopropylbenzenesulfonyl chloride, N-methylimidazole / 2.67 h

With pyridine; 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; hydrogen; triethylamine; palladium on activated charcoal; In hexane; chloroform;

Reference yield:

rac-1,2-dipalmitoylglycerol (1042289-75-7) → Hexadecanoic acid 2-{(2-chloro-phenoxy)-[(2R,3S,4S,5R)-5-(4-hexadecanoylamino-2-oxo-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-ylmethoxy]-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester (176776-97-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / Et₃N / CHCl₃ / 1.) ice bath, 20 min, 2.) r.t., 3,5 h

2: 42 percent / pyridine, 2,4,6-triisopropylbenzenesulfonyl chloride, N-methylimidazole / 2.67 h

With pyridine; 1-methyl-1H-imidazole; 2,4,6-triisopropylphenylsulfonyl chloride; triethylamine; In chloroform;

upstream raw materials:

(2-Chlorophenyl) (1,2-di-O-palmitoylglyceryl) phosphate

N⁴-Palmitoyl-1-β-D-arabinofuranosylcytosin

rac-1,2-dipalmitoylglycerol

1,2-di-O-palmitoyl-3-O-benzyl-rac-glycerol