(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

Base Information

Chemical Name:(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran
CAS No.:1146690-68-7
Molecular Formula:C₂₀H₃₀O₃
Molecular Weight:318.456
Hs Code.:

Synonyms:(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

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Chemical Property of (2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

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Technology Process of (2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

There total 8 articles about (2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran 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: 90.0%

: 1146690-87-0
(3S)-9-(benzyloxy)-3-(2-bromo-1-ethoxyethoxy)-1-nonyne

: 1146690-68-7
(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In benzene; for 0.5h; Inert atmosphere; Reflux;
DOI:10.1021/ol9002724

Reference yield:

: 1146690-66-5
{(2S,3S)-3-[6-(benzyloxy)hexyl]oxiran-2-yl}methanol

: 1146690-68-7
(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

Guidance literature:: Multi-step reaction with 4 steps

1: sodium hydrogencarbonate; triphenylphosphine / tetrachloromethane / 24 h / Inert atmosphere; Reflux

2: lithium; ferric nitrate / tetrahydrofuran; ammonia / -78 °C / Inert atmosphere; liquid NH₃

3: N-Bromosuccinimide / dichloromethane / 0 - 20 °C / Inert atmosphere

4: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 0.5 h / Inert atmosphere; Reflux

With N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; lithium; sodium hydrogencarbonate; ferric nitrate; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; benzene;
DOI:10.1002/ejoc.201001205

Reference yield:

: 1146690-85-8
(E)-9-(benzyloxy)-2-nonen-1-ol

: 1146690-68-7
(2S)-2-[6-(benzyloxy)hexyl]-5-ethoxy-3-methylenetetrahydrofuran

Guidance literature:: Multi-step reaction with 5 steps

1.1: titanium(IV) isopropylate; L-(+)-diisopropyl tartrate / dichloromethane; toluene / 0.5 h / -20 °C / Molecular sieve; Inert atmosphere

1.2: -20 - 0 °C / Molecular sieve; Inert atmosphere

2.1: sodium hydrogencarbonate; triphenylphosphine / tetrachloromethane / 24 h / Inert atmosphere; Reflux

3.1: lithium; ferric nitrate / tetrahydrofuran; ammonia / -78 °C / Inert atmosphere; liquid NH₃

4.1: N-Bromosuccinimide / dichloromethane / 0 - 20 °C / Inert atmosphere

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / benzene / 0.5 h / Inert atmosphere; Reflux

With titanium(IV) isopropylate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); L-(+)-diisopropyl tartrate; tri-n-butyl-tin hydride; lithium; sodium hydrogencarbonate; ferric nitrate; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; toluene; benzene; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation;
DOI:10.1002/ejoc.201001205