(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

Base Information

Chemical Name:(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene
CAS No.:1332850-52-8
Molecular Formula:C₃₁H₃₅FO₃
Molecular Weight:474.616
Hs Code.:

Synonyms:(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

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Chemical Property of (4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

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Technology Process of (4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

There total 4 articles about (4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene 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: 93.0%

: 1332850-50-6
(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-ol

: 100-39-0
benzyl bromide

: 1332850-52-8
(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

Guidance literature:: (4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-ol; With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; mineral oil; at 0 - 20 ℃; Inert atmosphere;

benzyl bromide; In tetrahydrofuran; mineral oil; at 0 ℃; Inert atmosphere;
DOI:10.1016/j.jfluchem.2011.05.031

Reference yield:

: 1309594-26-0
(5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-5-fluoroocta-2,7-dien-4-one

: 1332850-52-8
(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.33 h / 0 °C

2.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

2.2: 0 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; mineral oil;
DOI:10.1016/j.jfluchem.2011.05.031

Reference yield:

: 1309594-24-8
(2S,3S)-methyl 3-((S)-1,2-bis(benzyloxy)ethyl)-2-fluoropent-4-enoate

: 1332850-52-8
(4R,5S,6S,E)-6-((S)-1,2-bis(benzyloxy)ethyl)-4-benzyloxy-5-fluoroocta-2,7-diene

Guidance literature:: Multi-step reaction with 3 steps

1.1: trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride / dichloromethane

2.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 0.33 h / 0 °C

3.1: tetra-(n-butyl)ammonium iodide; sodium hydride / tetrahydrofuran; mineral oil / 0 - 20 °C / Inert atmosphere

3.2: 0 °C / Inert atmosphere

With sodium tetrahydroborate; cerium(III) chloride heptahydrate; trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; mineral oil;
DOI:10.1016/j.jfluchem.2011.05.031