(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

Base Information

Chemical Name:(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid
CAS No.:905910-48-7
Molecular Formula:C₃₀H₅₂O₅
Molecular Weight:492.74
Hs Code.:

Synonyms:(2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

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Chemical Property of (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

Chemical Property:

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Technology Process of (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid

There total 7 articles about (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoic acid 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: 100.0%

: 1376112-94-5
benzyl (2S,3S,5R)-5-(4-methoxybenzyloxy)-2-hexyl-3-hydroxyhexadecanoate

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

Guidance literature:: With water; lithium hydroxide; In tetrahydrofuran; methanol; at 20 - 55 ℃; for 2h; Inert atmosphere;
DOI:10.1021/jo300139r

Reference yield:

: 112-54-9
Dodecanal

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

Guidance literature:: Multi-step reaction with 8 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

With n-butyllithium; titanium(IV) dichlorodiisopropylate; (S)-(-)-2-phenyl-2,3-dihydrobenzo[d]imidazo[2,1-b]thiazole; water; 2,2-dimethylpropanoic anhydride; sodium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; lithium hydroxide; lithium hexamethyldisilazane; benzo[1,3,2]dioxaborole; In tetrahydrofuran; methanol; diethyl ether; hexane; 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

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

Guidance literature:: Multi-step reaction with 6 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

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