hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester

Base Information

• Chemical Name: hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester
• CAS No.: 607358-66-7
• Molecular Formula: C₆₁H₉₆NO₁₂P
• Molecular Weight: 1066.41
• Mol file: 607358-66-7.mol

Synonyms:hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester

Chemical Property of hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester

There total 7 articles about hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-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: 71.0%

1-hexadecylcarboxylic acid (57-10-3) + (2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester (607358-65-6) → hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester (607358-66-7)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In dichloromethane; for 18h;

DOI:10.1021/jo011185a

Reference yield:

benzyl 2-hydroxyethylcarbamate (77987-49-6) → hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester (607358-66-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 1-H-tetrazole / CH₂Cl₂ / 3 h / 20 °C

2: tetrazole / CH₂Cl₂ / 2 h / 20 °C

3: 1.033 g / m-CPBA / CH₂Cl₂ / 1 h

4: 65 percent / HCl / tetrahydrofuran / 3 h / 20 °C

5: 71 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 18 h

With 1H-tetrazole; hydrogenchloride; dmap; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo011185a

Reference yield:

benzyl-N,N,N',N'-tetraisopropylphosphorodiamidite (108549-21-9) → hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-(4'-methoxy-benzyloxymethyl)}-propyl ester (607358-66-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 68 percent / 1-H-tetrazole / CH₂Cl₂ / 3 h / 20 °C

2: tetrazole / CH₂Cl₂ / 2 h / 20 °C

3: 1.033 g / m-CPBA / CH₂Cl₂ / 1 h

4: 65 percent / HCl / tetrahydrofuran / 3 h / 20 °C

5: 71 percent / dicyclohexylcarbodiimide; 4-dimethylaminopyridine / CH₂Cl₂ / 18 h

With 1H-tetrazole; hydrogenchloride; dmap; 3-chloro-benzenecarboperoxoic acid; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo011185a

upstream raw materials:

1-hexadecylcarboxylic acid

(2-{benzyloxy-[(2R,3R)-2,3-dihydroxy-4-(4'-methoxybenzyloxymethyl)-butoxy]-phosphoryloxy}-ethyl)-carbamic acid benzyl ester

benzyl 2-hydroxyethylcarbamate

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

Downstream raw materials:

hexadecanoic acid {(1R,2R)-1-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxymethyl]-3-(benzyloxy-diisopropylamino-phosphanyloxy)-2-hexanoyloxy}-propyl ester

hexadecanoic acid {(1R,2R)-3-[benzyloxy-(2-benzyloxycarbonylamino-ethoxy)-phosphoryloxy]-2-hexadecanoyloxy-1-hydroxymethyl}-propyl ester