(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

Base Information

Chemical Name:(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether
CAS No.:1374015-19-6
Molecular Formula:C₃₈H₆₄O₄
Molecular Weight:584.924
Hs Code.:

Synonyms:(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

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Chemical Property of (S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

Chemical Property:

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Technology Process of (S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

There total 14 articles about (S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether 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:

: 1374015-18-5
(S,11E,19Z)-11,19-octacosadiene-1,3-diol 1-PMB ether

: 108-24-7
acetic anhydride

: 1374015-19-6
(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

Guidance literature:: With pyridine; dmap; at 20 ℃;
DOI:10.1016/j.tet.2012.03.002

Reference yield:

: 1374015-09-4
(S)-3-tert-butyldimethylsilyloxy-11-dodecyn-1-ol PMB ether

: 1374015-19-6
(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / -65 - -10 °C / Inert atmosphere

1.2: -65 - 20 °C / Inert atmosphere; Reflux

2.1: lithium aluminium tetrahydride / tetrahydrofuran; diethylene glycol dimethyl ether / 48 h / 10 - 140 °C / Inert atmosphere

2.2: Inert atmosphere; Cooling with ice

3.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

3.2: 5 h / 20 - 50 °C / Inert atmosphere

4.1: pyridine; dmap / 20 °C

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; diethylene glycol dimethyl ether; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.03.002

Reference yield:

: 822-21-9
hexadec-7-yn-1-ol

: 1374015-19-6
(S,11E,19Z)-3-acetoxy11,19-octacosadiene-1ol 1-PMB ether

Guidance literature:: Multi-step reaction with 7 steps

1.1: quinoline; hydrogen / cyclohexane / 2 h / 20 °C / 760.05 Torr

2.1: pyridine / 4 h / 0 - 5 °C

3.1: sodium iodide / N,N-dimethyl-formamide / 5 h / 80 °C

4.1: n-butyllithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane / -65 - -10 °C / Inert atmosphere

4.2: -65 - 20 °C / Inert atmosphere; Reflux

5.1: lithium aluminium tetrahydride / tetrahydrofuran; diethylene glycol dimethyl ether / 48 h / 10 - 140 °C / Inert atmosphere

5.2: Inert atmosphere; Cooling with ice

6.1: potassium tert-butylate / tetrahydrofuran; N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere

6.2: 5 h / 20 - 50 °C / Inert atmosphere

7.1: pyridine; dmap / 20 °C

With pyridine; quinoline; dmap; lithium aluminium tetrahydride; n-butyllithium; potassium tert-butylate; hydrogen; sodium iodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; hexane; diethylene glycol dimethyl ether; cyclohexane; N,N-dimethyl-formamide;
DOI:10.1016/j.tet.2012.03.002