Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester

Base Information

• Chemical Name: Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester
• CAS No.: 228406-19-7
• Molecular Formula: C₃₆H₆₄NO₆P
• Molecular Weight: 637.881

Synonyms:Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester

Chemical Property of Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester

Chemical Property:

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Technology Process of Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester

There total 4 articles about Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl 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: 82.0%

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) + 2-O-Acetyl-1-O-octadecanoyl-sn-glycerin (83542-44-3) → Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester (228406-19-7)

Guidance literature:

With 1H-tetrazole; In dichloromethane;

DOI:10.1016/S0040-4039(98)02151-0

Reference yield:

3-O-Benzyl-1-O-octadecanoyl-sn-glycerin (4145-51-1,6236-22-2,116947-35-4,988-76-1) → Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester (228406-19-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / N,N-dimethylaminopyridine / pyridine; CH₂Cl₂ / 0 - 20 °C

2: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C

3: 82 percent / 1H-tetrazole / CH₂Cl₂ / 20 °C

With 1H-tetrazole; dmap; hydrogen; palladium on activated charcoal; In pyridine; dichloromethane; ethyl acetate; 1: Acetylation / 2: Hydrogenolysis / 3: Substitution;

DOI:10.1016/S0040-4020(00)00161-7

Reference yield:

2-O-Acetyl-3-O-benzyl-1-O-octadecanoyl-sn-glycerin (83526-65-2) → Octadecanoic acid (R)-2-acetoxy-3-(benzyloxy-diisopropylamino-phosphanyloxy)-propyl ester (228406-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / H₂ / Pd/C / ethyl acetate / 20 °C

2: 82 percent / 1H-tetrazole / CH₂Cl₂ / 20 °C

With 1H-tetrazole; hydrogen; palladium on activated charcoal; In dichloromethane; ethyl acetate; 1: Hydrogenolysis / 2: Substitution;

DOI:10.1016/S0040-4020(00)00161-7

upstream raw materials:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite

2-O-Acetyl-1-O-octadecanoyl-sn-glycerin

3-O-Benzyl-1-O-octadecanoyl-sn-glycerin

Stearoyl chloride

Downstream raw materials:

Octadecanoic acid (R)-2-acetoxy-3-{benzyloxy-[(1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-tris-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryloxy}-propyl ester

Octadecanoic acid (R)-2-acetoxy-3-[benzyloxy-((1S,2R,3R,4S,5S,6R)-2,6-bis-benzyloxymethoxy-3,4,5-trihydroxy-cyclohexyloxy)-phosphoryloxy]-propyl ester

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