(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

Base Information

Chemical Name:(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide
CAS No.:905910-49-8
Molecular Formula:C₃₀H₅₀O₄
Molecular Weight:474.725
Hs Code.:

Synonyms:(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

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Chemical Property of (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

Chemical Property:

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Technology Process of (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

There total 8 articles about (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide 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: 91.0%

: 905910-48-7
(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

: 905910-49-8
(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

Guidance literature:: With dmap; 2-methyl-6-nitrobenzoic anhydride; sodium hydrogencarbonate; triethylamine; In dichloromethane; water; at 0 - 20 ℃; for 12h; Inert atmosphere;
DOI:10.1021/jo300139r

Reference yield:

: 112-54-9
Dodecanal

: 905910-49-8
(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

Guidance literature:: Multi-step reaction with 9 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 - -23 °C / Inert atmosphere

1.2: 1 h / -78 - -23 °C / Inert atmosphere

2.1: potassium carbonate / methanol / 1 h / 20 °C / Inert atmosphere

3.1: (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine / diethyl ether / 12 h / 20 °C / Inert atmosphere; Resolution of racemate

4.1: sodium hydride / N,N-dimethyl-formamide; paraffin / 1 h / 0 °C / Inert atmosphere

4.2: 0.67 h / 0 - 20 °C / Inert atmosphere

5.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 3.5 h / 0 - 70 °C / Inert atmosphere

5.2: 0.17 h / 0 °C / pH 7 / Inert atmosphere; aq. phosphate buffer

5.3: 3 h / 20 °C / Inert atmosphere

6.1: titanium(IV) dichlorodiisopropylate / toluene / 0.25 h / -78 °C / Inert atmosphere

6.2: 4 h / -78 °C / Inert atmosphere

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 - -45 °C / Inert atmosphere

7.2: 3 h / -45 °C / Inert atmosphere

8.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 - 55 °C / Inert atmosphere

9.1: dmap; 2-methyl-6-nitrobenzoic anhydride; sodium hydrogencarbonate; triethylamine / dichloromethane; water / 12 h / 0 - 20 °C / Inert atmosphere

With dmap; n-butyllithium; titanium(IV) dichlorodiisopropylate; (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2-methyl-6-nitrobenzoic anhydride; water; 2,2-dimethylpropanoic anhydride; sodium hydride; sodium hydrogencarbonate; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin; 6.1: Mukaiyama aldol reaction;
DOI:10.1021/jo300139r

Reference yield:

: 73501-38-9,77889-04-4,136022-04-3
(±)-tetradec-1-yn-3-ol

: 905910-49-8
(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyldecan-3-olide

Guidance literature:: Multi-step reaction with 7 steps

1.1: (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2,2-dimethylpropanoic anhydride; N-ethyl-N,N-diisopropylamine / diethyl ether / 12 h / 20 °C / Inert atmosphere; Resolution of racemate

2.1: sodium hydride / N,N-dimethyl-formamide; paraffin / 1 h / 0 °C / Inert atmosphere

2.2: 0.67 h / 0 - 20 °C / Inert atmosphere

3.1: benzo[1,3,2]dioxaborole / tetrahydrofuran / 3.5 h / 0 - 70 °C / Inert atmosphere

3.2: 0.17 h / 0 °C / pH 7 / Inert atmosphere; aq. phosphate buffer

3.3: 3 h / 20 °C / Inert atmosphere

4.1: titanium(IV) dichlorodiisopropylate / toluene / 0.25 h / -78 °C / Inert atmosphere

4.2: 4 h / -78 °C / Inert atmosphere

5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / -78 - -45 °C / Inert atmosphere

5.2: 3 h / -45 °C / Inert atmosphere

6.1: water; lithium hydroxide / tetrahydrofuran; methanol / 2 h / 20 - 55 °C / Inert atmosphere

7.1: dmap; 2-methyl-6-nitrobenzoic anhydride; sodium hydrogencarbonate; triethylamine / dichloromethane; water / 12 h / 0 - 20 °C / Inert atmosphere

With dmap; titanium(IV) dichlorodiisopropylate; (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; 2-methyl-6-nitrobenzoic anhydride; water; 2,2-dimethylpropanoic anhydride; sodium hydride; sodium hydrogencarbonate; triethylamine; N-ethyl-N,N-diisopropylamine; lithium hydroxide; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; paraffin; 4.1: Mukaiyama aldol reaction;
DOI:10.1021/jo300139r