2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic acid

Base Information

• Chemical Name: 2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic acid
• CAS No.: 112763-98-1
• Molecular Formula: C₂₉H₅₀O₄
• Molecular Weight: 462.714
• European Community (EC) Number: 601-200-6
• DSSTox Substance ID: DTXSID501220369
• Mol file: 112763-98-1.mol

Synonyms:112763-98-1;2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic acid;SCHEMBL8780213;DTXSID501220369;Hexadecanoic acid, 2-hexyl-3-hydroxy-5-(phenylmethoxy)-

Chemical Property of 2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic acid

Chemical Property:

• Vapor Pressure: 3.61E-15mmHg at 25°C
• XLogP3: 9.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 22
• Exact Mass: 462.37091007
• Heavy Atom Count: 33
• Complexity: 447

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCC(CC(C(CCCCCC)C(=O)O)O)OCC1=CC=CC=C1

Technology Process of 2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic acid

There total 1 articles about 2-Hexyl-3-hydroxy-5-(phenylmethoxy)hexadecanoic 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:

→ rac-(2RS,3RS,5SR)-5-benzyloxy-2-hexyl-3-hydroxyhexadecanoic acid (112763-98-1)

Guidance literature:

Reference yield:

(5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid (112763-98-1,114299-20-6,134453-13-7,136890-13-6) → (3S,4S)-3-hexyl-4-[(R)-2-hydroxytridecyl]-2-oxetanone (68711-40-0,104871-99-0,104872-00-6,104872-03-9,104872-05-1,104872-07-3,104872-19-7,104872-06-2)

Guidance literature:

Multi-step reaction with 10 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature

2: p-TsOH, / CHCl₃ / Ambient temperature

3: Jones' reagent / acetone / 1 h / 10 °C

4: 84 percent / H₂ / PtO₂ / ethyl acetate / 48 h / 37503 Torr / Ambient temperature

5: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

6: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

7: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

8: H₂ / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

9: benzenesulfonylchloride, pyridine / 0 °C

10: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C

With pyridine; potassium hydroxide; jones' reagent; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; benzenesulfonyl chloride; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; acetone;

DOI:10.1021/jo00241a018

Reference yield:

(5R)-5-(benzyloxy)-3-hydroxy-2-hexylhexadecanoic acid (112763-98-1,114299-20-6,134453-13-7,136890-13-6) → Orlistat (104872-04-0,104872-27-7,104872-28-8,111466-61-6,111466-62-7,111466-63-8,130193-40-7,130193-41-8,130193-42-9,130193-43-0,96829-58-2,1225451-00-2)

Guidance literature:

Multi-step reaction with 11 steps

1: H₂ / 10percent Pd/C / tetrahydrofuran / 760 Torr / Ambient temperature

2: p-TsOH, / CHCl₃ / Ambient temperature

3: Jones' reagent / acetone / 1 h / 10 °C

4: 84 percent / H₂ / PtO₂ / ethyl acetate / 48 h / 37503 Torr / Ambient temperature

5: 73 percent / CF₃SO₃H / CH₂Cl₂ / 2 h / 0 - 20 °C

6: 1.) 1 N KOH / 1.) dioxane, water, RT, 5 h, 2.) THF, HMPA, 24 h

7: 73 percent / p-toluenesulfonic acid / CH₂Cl₂ / 3 h / -10 - 20 °C

8: H₂ / 10percent Pd/C / tetrahydrofuran / 4 h / 760 Torr / Ambient temperature

9: benzenesulfonylchloride, pyridine / 0 °C

10: 88 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 50 - 55 °C

11: 80 percent / triphenylphosphine, diethyl azodicarboxylate / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; potassium hydroxide; jones' reagent; trifluorormethanesulfonic acid; hydrogen; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; benzenesulfonyl chloride; triphenylphosphine; diethylazodicarboxylate; platinum(IV) oxide; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; chloroform; ethyl acetate; acetone;

DOI:10.1021/jo00241a018

Downstream raw materials:

(3S,4S)-3-hexyl-4-[(2S)-2-hydroxytridecyl]oxetan-2-one

(3S,4S,6R)-3-Hexyl-3,4,5,6-tetrahydro-4-hydroxy-6-undecyl-2H-pyran-2-one

Orlistat

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

Refernces