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

Base Information

• Chemical Name: Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester
• CAS No.: 404893-46-5
• Molecular Formula: C₆₀H₈₅O₁₄P
• Molecular Weight: 1061.3

Synonyms:Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester

Chemical Property of Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester

Chemical Property:

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Technology Process of Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester

There total 12 articles about Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-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: 52.0%

Octadecanoic acid (R)-3-{benzyloxy-[(1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-bis-(4-methoxy-benzyloxy)-cyclohexyloxy]-phosphoryloxy}-2-butyryloxy-propyl ester (404893-44-3) → Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester (404893-46-5)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 2.5h;

DOI:10.1016/S0040-4039(01)01946-3

Reference yield:

(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-prop-2-en-1-ol (106221-09-4) → Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester (404893-46-5)

Guidance literature:

Multi-step reaction with 12 steps

1: 95 percent / NaH / dimethylformamide

2: 92 percent / 80 percent AcOH / 48 h / 70 °C

3: 68 percent / n-BuLi / diethyl ether / 20 °C

4: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 20 °C

5: 92 percent / NaH / dimethylformamide

6: 98 percent / OsO₄; quinuclidine; NMO / CH₂Cl₂ / 20 °C

7: DMAP / pyridine

8: 30 percent / diisopropylethylamine; n-Bu₄NBr / CH₂Cl₂ / 48 h / 70 °C

9: 100 percent / K₂CO₃ / methanol / 4 h / 20 °C

10: 1H-tetrazole / CH₂Cl₂ / 2.5 h / 20 °C

11: m-CPBA / CH₂Cl₂ / 0.75 h / -78 - 20 °C

12: 52 percent / DDQ / CH₂Cl₂; H₂O / 2.5 h / 20 °C

With Quinuclidine; 1H-tetrazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutylammomium bromide; sodium hydride; potassium carbonate; acetic acid; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 3: Wittig methylenation;

DOI:10.1016/S0040-4039(01)01946-3

Reference yield:

(3R,4R,5R)-4-Benzyloxy-5-((S)-1-benzyloxy-allyl)-tetrahydro-furan-2,3-diol → Octadecanoic acid (R)-3-[benzyloxy-((1S,2R,3S,4S,5R,6R)-2,4-bis-benzyloxy-6-benzyloxymethoxy-3,5-dihydroxy-cyclohexyloxy)-phosphoryloxy]-2-butyryloxy-propyl ester (404893-46-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 68 percent / n-BuLi / diethyl ether / 20 °C

2: 85 percent / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 1 h / 20 °C

3: 92 percent / NaH / dimethylformamide

4: 98 percent / OsO₄; quinuclidine; NMO / CH₂Cl₂ / 20 °C

5: DMAP / pyridine

6: 30 percent / diisopropylethylamine; n-Bu₄NBr / CH₂Cl₂ / 48 h / 70 °C

7: 100 percent / K₂CO₃ / methanol / 4 h / 20 °C

8: 1H-tetrazole / CH₂Cl₂ / 2.5 h / 20 °C

9: m-CPBA / CH₂Cl₂ / 0.75 h / -78 - 20 °C

10: 52 percent / DDQ / CH₂Cl₂; H₂O / 2.5 h / 20 °C

With Quinuclidine; 1H-tetrazole; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; tetrabutylammomium bromide; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Grubbs catalyst first generation; In pyridine; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; 1: Wittig methylenation;

DOI:10.1016/S0040-4039(01)01946-3

upstream raw materials:

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

(S)-1-((3aR,5R,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-prop-2-en-1-ol

(1R,2R,3S,6S)-2,6-Bis-benzyloxy-cyclohex-4-ene-1,3-diol

(3aR,5R,6S,6aR)-6-Benzyloxy-5-((S)-1-benzyloxy-allyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole

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