(2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal

Base Information

• Chemical Name: (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal
• CAS No.: 244628-37-3
• Molecular Formula: C₂₉H₄₈O₃
• Molecular Weight: 444.698
• Mol file: 244628-37-3.mol

Synonyms:(2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal

Chemical Property of (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal

There total 6 articles about (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal 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:

(2S,3S,3aS,4aS,5R,8S,8aR,2'R,1E)-2-(2'phenylmethyloxy-tridecyl)-3-(1-hexenyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole (244628-36-2) → (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal (244628-37-3) + (1S,3S,4R)-3-hydroxy-4,7,7-trimethylbicyclo[2.2.1]heptan-2-one (23963-16-8)

Guidance literature:

(2S,3S,3aS,4aS,5R,8S,8aR,2'R,1"E)-2-(2'phenylmethyloxy-tridecyl)-3-(1"-hexenyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole; With 3-chloro-benzenecarboperoxoic acid; In diethyl ether; at 20 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Further stages.;

DOI:10.1021/ol990734k

Reference yield:

(2S,3S,3aS,4aS,5R,8S,8aR,2'R)-2-(2'-phenylmethyloxy-tridecyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]benzoxazole-3-carboxylic acid ethyl ester (244628-34-0) → (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal (244628-37-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 76 percent / DIBAH / toluene / 1 h / -78 °C

2.1: sodium amide / tetrahydrofuran / 4 h / Heating

2.2: tetrahydrofuran / -78 °C

3.1: mCPBA / diethyl ether / 1 h / 20 °C

3.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

With diisobutylaluminium hydride; sodium amide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1021/ol990734k

Reference yield:

(2S,3S,3aS,4aS,5R,8S,8aR,2'R)-2-(2'-phenylmethyloxy-tridecyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole-3-carboxaldehyde (244628-35-1) → (2S,3S,5R,1'E)-2-(1'-hexenyl)-3-hydroxy-5-phenylmethyloxy-hexadecanal (244628-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium amide / tetrahydrofuran / 4 h / Heating

1.2: tetrahydrofuran / -78 °C

2.1: mCPBA / diethyl ether / 1 h / 20 °C

2.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

With sodium amide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol990734k

upstream raw materials:

(2S,3S,3aS,4aS,5R,8S,8aR,2'R,1E)-2-(2'phenylmethyloxy-tridecyl)-3-(1-hexenyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole

(2S,3S,3aS,4aS,5R,8S,8aR,2'R)-2-(2'-phenylmethyloxy-tridecyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]benzoxazole-3-carboxylic acid ethyl ester

(2S,3S,3aS,4aS,5R,8S,8aR,2'R)-2-(2'-phenylmethyloxy-tridecyl)-5,10,10-trimethyl-5,8-methano-octahydro-2H-isoxazolo-[3,2-b]-benzoxazole-3-carboxaldehyde

pentylidenetriphenylphosphorane

Downstream raw materials:

(3S,4S,2'R,1Z)-3-(1-hexenyl)-4-(2'-phenylmethyloxy-tridecyl)-2-oxetanone

Orlistat

(3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone