Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

Base Information

• Chemical Name: Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester
• CAS No.: 162792-26-9
• Molecular Formula: C₇₆H₁₀₉O₁₂P
• Molecular Weight: 1245.67

Synonyms:Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

Chemical Property of Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

Chemical Property:

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Technology Process of Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester

There total 13 articles about Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-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: 90.0%

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphanyloxy]-1-hexadecanoyloxymethyl-ethyl ester (162792-25-8) → Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester (162792-26-9)

Guidance literature:

With tert.-butylhydroperoxide; In dichloromethane; 1.) 0 deg C, 90 min, 2.) room temperature, 1 h;

DOI:10.1016/S0040-4020(97)10003-5

Reference yield:

(3aR,4R,5S,6R,7aR)-4,5,6-Tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole (162792-19-0) → Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester (162792-26-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 97 percent / conc. HCl / methanol / 48 h / Ambient temperature

2: 1.) Bu₂SnO / 1.) MeOH, reflux, 2 h, 2.) DMF, toluene, 0 deg C, 1 h

3: 73 percent / NaH, Bu₄NI / dimethylformamide / Ambient temperature

4: 77 percent / conc. HCl / methanol / 2 h / Heating

5: 100 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 24 h / Ambient temperature

6: 60 percent / tetrazole / CH₂Cl₂; acetonitrile / 20 h / Ambient temperature

7: 90 percent / tert-BuOOH / CH₂Cl₂ / 1.) 0 deg C, 90 min, 2.) room temperature, 1 h

With 1H-tetrazole; hydrogenchloride; tert.-butylhydroperoxide; N,N-diisopropylamine tetrazolide; tetra-(n-butyl)ammonium iodide; sodium hydride; di(n-butyl)tin oxide; In methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0040-4020(97)10003-5

Reference yield:

Diisopropyl-phosphoramidous acid benzyl ester (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyl ester (162792-24-7) → Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphoryloxy]-1-hexadecanoyloxymethyl-ethyl ester (162792-26-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / tetrazole / CH₂Cl₂; acetonitrile / 20 h / Ambient temperature

2: 90 percent / tert-BuOOH / CH₂Cl₂ / 1.) 0 deg C, 90 min, 2.) room temperature, 1 h

With 1H-tetrazole; tert.-butylhydroperoxide; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(97)10003-5

upstream raw materials:

Hexadecanoic acid (R)-2-[benzyloxy-((1R,2R,3S,4R,6R)-2,3,4,6-tetrakis-benzyloxy-cyclohexyloxy)-phosphanyloxy]-1-hexadecanoyloxymethyl-ethyl ester

1,2-dipalmitoyl-sn-glycerol

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

(1R,2R,3S,4S,5R)-3,4,5-Tris-benzyloxy-cyclohexane-1,2-diol

Downstream raw materials:

1D-3-deoxyphosphatidylinositol

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