methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate

Base Information

• Chemical Name: methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate
• CAS No.: 114299-23-9
• Molecular Formula: C₃₀H₅₈O₅
• Molecular Weight: 498.788
• Mol file: 114299-23-9.mol

Synonyms:methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate

Chemical Property of methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate

There total 1 articles about methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate 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:

Oleic aldehyde (2423-10-1) → methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate (114299-23-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -112 °C

2: methanol / 1 h / Ambient temperature

3: 74.5 percent / TsOH / CH₂Cl₂ / 0.75 h / 0 °C

4: 91 percent / DIBAH / CH₂Cl₂; toluene / 0.58 h / -70 °C

5: 77 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -118 °C

6: 89.4 percent / methanol / 0.5 h / Ambient temperature

7: 75 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -50 deg C, 15 min; 2.) room temp. 3 h

8: 97.5 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature

With n-butyllithium; hydrogen; diisobutylaluminium hydride; toluene-4-sulfonic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; toluene;

DOI:10.1002/hlca.19870700522

Reference yield:

methyl (2S,3S,5S)-2-ethyl-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>dodecosanoate (114299-23-9) → (S)-1'-<<(2''S,3''S)-3''-ethyl-4''-oxooxetan-2''-yl>methyl>octadecyl (S)-N-<(benzyloxy)carbonyl>leucinate

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / KOH/MeOH / 19 h / Ambient temperature

2: 71 percent / benzenesulfonyl chloride / pyridine / 22 h / 5 °C

3: 55 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 55 °C

4: 63.5 percent / 1.) DCC; 2.) p-(dimethylamino)pyridine / dimethylformamide / 0.5 h / Ambient temperature

With methanol; dmap; potassium hydroxide; pyridinium p-toluenesulfonate; benzenesulfonyl chloride; dicyclohexyl-carbodiimide; In pyridine; ethanol; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19870700522

upstream raw materials:

Oleic aldehyde