(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

Base Information

Chemical Name:(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate
CAS No.:1574334-62-5
Molecular Formula:C₂₈H₄₂O₅
Molecular Weight:458.638
Hs Code.:

Synonyms:(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

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Chemical Property of (E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

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Technology Process of (E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

There total 11 articles about (E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate 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: 72.2%

: 1574334-34-1
benzyl tetradec-13-enoate

: 1574334-36-3
(S)-2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-hydroxyethyl-4-methylbenzenesulfonate

: 1574334-62-5
(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

Guidance literature:: benzyl tetradec-13-enoate; (S)-2-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-2-hydroxyethyl-4-methylbenzenesulfonate; With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; for 10h; Reflux;

With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1039/c3ob42364f

Reference yield:

: 92936-93-1
(4R,5S)-4-(bis(ethylthio)methyl)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-1,3-dioxolane

: 1574334-62-5
(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: mercury(II) oxide; mercury dichloride / water; acetone / 60 °C

2: potassium tert-butylate / tetrahydrofuran / 1 h / 0 - 20 °C

3: acetic acid / water / 20 °C

4: triethylamine; di(n-butyl)tin oxide / dichloromethane / 20 °C

5: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 10 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; potassium tert-butylate; di(n-butyl)tin oxide; acetic acid; triethylamine; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; water; acetone;
DOI:10.1039/c3ob42364f

Reference yield:

: 22893-94-3
(4R,5S)-4-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-5-vinyl-1,3-dioxolane

: 1574334-62-5
(E)-benzyl-14-((4S,5R)-2,2-dimethyl-5-((R)-oxiran-2-yl)-1,3-dioxolan-4-yl)tetradec-13-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: acetic acid / water / 20 °C

2: triethylamine; di(n-butyl)tin oxide / dichloromethane / 20 °C

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 10 h / Reflux

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; di(n-butyl)tin oxide; acetic acid; triethylamine; In dichloromethane; water;
DOI:10.1039/c3ob42364f