(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

Base Information

Chemical Name:(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one
CAS No.:322765-08-2
Molecular Formula:C₂₅H₃₈O₆
Molecular Weight:434.573
Hs Code.:

Synonyms:(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

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Chemical Property of (5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

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Technology Process of (5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

There total 12 articles about (5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one 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: 66.0%

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

: 322765-08-2
(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

Guidance literature:: (S)-2-[(S)-1-Hydroxy-2-(tetrahydro-pyran-2-yloxy)-propyl]-12-(4-methoxy-benzyloxy)-5-methoxymethoxy-dodecanoic acid methyl ester; With acetic acid; In tetrahydrofuran; water; at 55 ℃; for 2h;

With triethylamine; trifluoroacetic anhydride; In dichloromethane; at 20 ℃; for 20h; Further stages.;
DOI:10.1021/jo005643b

Reference yield:

: 629-11-8
1,6-hexanediol

: 322765-08-2
(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 44 percent / NaH / dimethylformamide / 2 h / -20 °C

2.1: 93 percent / CBr₄; PPh₃ / CH₂Cl₂ / 1 h / 20 °C

3.1: acetonitrile / 48 h / 90 °C

4.1: 64 percent / tetrahydrofuran / 2 h / -78 °C

5.1: 97 percent / H₂; Et₃N / 10percent Pd/C / ethanol / 3 h / 20 °C / 760.05 Torr

6.1: 96 percent / i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

7.1: AcOH / tetrahydrofuran; H₂O / 2 h / 55 °C

7.2: 66 percent / Et₃N; (CF₃CO)2O / CH₂Cl₂ / 20 h / 20 °C

With n-butyllithium; carbon tetrabromide; hydrogen; sodium hydride; acetic acid; triethylamine; diisopropylamine; triphenylphosphine; 10percent Pd/C; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 4.1: Wittig reaction;
DOI:10.1021/jo005643b

Reference yield:

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

: 322765-08-2
(5S,3'S)-3-(3'-methoxymethoxy-10'-p-methoxybenzyloxydodecan-1'-yl)-5-methylfuran-2(5H)-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: 91 percent / diisopropylethylamine / CH₂Cl₂ / 12 h / 0 - 20 °C

2.1: 68 percent / H₅IO₆ / diethyl ether / 12 h / 20 °C

3.1: 64 percent / tetrahydrofuran / 2 h / -78 °C

4.1: 97 percent / H₂; Et₃N / 10percent Pd/C / ethanol / 3 h / 20 °C / 760.05 Torr

5.1: 96 percent / i-Pr₂NH; BuLi / tetrahydrofuran; hexane / 1.5 h / -78 °C

6.1: AcOH / tetrahydrofuran; H₂O / 2 h / 55 °C

6.2: 66 percent / Et₃N; (CF₃CO)2O / CH₂Cl₂ / 20 h / 20 °C

With n-butyllithium; hydrogen; acetic acid; periodic acid; triethylamine; diisopropylamine; N-ethyl-N,N-diisopropylamine; 10percent Pd/C; In tetrahydrofuran; diethyl ether; ethanol; hexane; dichloromethane; water; 3.1: Wittig reaction;
DOI:10.1021/jo005643b