(3S)-9-(benzyloxy)-1-nonyn-3-ol

Base Information

Chemical Name:(3S)-9-(benzyloxy)-1-nonyn-3-ol
CAS No.:1146690-67-6
Molecular Formula:C₁₆H₂₂O₂
Molecular Weight:246.349
Hs Code.:

Synonyms:(3S)-9-(benzyloxy)-1-nonyn-3-ol

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Chemical Property of (3S)-9-(benzyloxy)-1-nonyn-3-ol

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Technology Process of (3S)-9-(benzyloxy)-1-nonyn-3-ol

There total 6 articles about (3S)-9-(benzyloxy)-1-nonyn-3-ol 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: 96.0%

: 1146690-86-9
(2S,3R)-2-[6-(benzyloxy)hexyl]-3-(chloromethyl)oxirane

: 1146690-67-6
(3S)-9-(benzyloxy)-1-nonyn-3-ol

Guidance literature:: (2S,3R)-2-[6-(benzyloxy)hexyl]-3-(chloromethyl)oxirane; With lithium amide; In tetrahydrofuran; ammonia; at -78 ℃; for 2h; liquid NH₃;

With ammonium chloride; In tetrahydrofuran; ammonia; liquid NH₃;
DOI:10.1021/ol9002724

Reference yield:

: 1146690-65-4
ethyl (E)-9-(benzyloxy)-2-nonenoate

: 1146690-67-6
(3S)-9-(benzyloxy)-1-nonyn-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: lithium aluminium tetrahydride; aluminum (III) chloride / diethyl ether / 1.17 h / 0 °C / Inert atmosphere

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

2.2: -20 - 0 °C / Molecular sieve; Inert atmosphere

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

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

With titanium(IV) isopropylate; aluminum (III) chloride; lithium aluminium tetrahydride; L-(+)-diisopropyl tartrate; lithium; sodium hydrogencarbonate; ferric nitrate; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; diethyl ether; dichloromethane; ammonia; toluene; 2.1: Sharpless epoxidation / 2.2: Sharpless epoxidation;
DOI:10.1002/ejoc.201001205

Reference yield:

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

: 1146690-67-6
(3S)-9-(benzyloxy)-1-nonyn-3-ol

Guidance literature:: Multi-step reaction with 3 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

With titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; lithium; sodium hydrogencarbonate; ferric nitrate; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; dichloromethane; ammonia; toluene; 1.1: Sharpless epoxidation / 1.2: Sharpless epoxidation;
DOI:10.1002/ejoc.201001205