(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

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Chemical Name:(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester
CAS No.:324024-12-6
Molecular Formula:C₃₁H₅₂O₉
Molecular Weight:568.748
Hs Code.:

Synonyms:(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

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Chemical Property of (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

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Technology Process of (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

There total 11 articles about (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl 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: 96.0%

: 76438-34-1
(S)-2-(tetrahydropyranyloxy)propanal

: 322765-07-1
methyl (5S)-5-methoxymethoxy-12-p-methoxybenzyloxydodecanoate

: 324024-12-6
(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

Guidance literature:: With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 1.5h;
DOI:10.1021/jo005643b

Reference yield:

: 629-11-8
1,6-hexanediol

: 324024-12-6
(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 44 percent / NaH / dimethylformamide / 2 h / -20 °C

2: 93 percent / CBr₄; PPh₃ / CH₂Cl₂ / 1 h / 20 °C

3: acetonitrile / 48 h / 90 °C

4: 64 percent / tetrahydrofuran / 2 h / -78 °C

5: 97 percent / H₂; Et₃N / 10percent Pd/C / ethanol / 3 h / 20 °C / 760.05 Torr

6: 96 percent / i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

With n-butyllithium; carbon tetrabromide; hydrogen; sodium hydride; triethylamine; diisopropylamine; triphenylphosphine; 10percent Pd/C; In tetrahydrofuran; ethanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 4: Wittig reaction;
DOI:10.1021/jo005643b

Reference yield:

: 79308-47-7
methyl (5R,6R)-6,7-O-isopropylidene-5,6,7-trihydroxy-heptanoate

: 324024-12-6
(S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 0 - 20 °C

2: 68 percent / H₅IO₆ / diethyl ether / 12 h / 20 °C

3: 64 percent / tetrahydrofuran / 2 h / -78 °C

4: 97 percent / H₂; Et₃N / 10percent Pd/C / ethanol / 3 h / 20 °C / 760.05 Torr

5: 96 percent / i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

With n-butyllithium; hydrogen; periodic acid; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; 3: Wittig reaction;
DOI:10.1021/jo005643b