methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate

Base Information

• Chemical Name: methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate
• CAS No.: 104802-42-8
• Molecular Formula: C₂₆H₄₈O₄
• Molecular Weight: 424.665
• Mol file: 104802-42-8.mol

Synonyms:methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate

Chemical Property of methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate

There total 1 articles about methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate 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 (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate (104802-42-8)

Guidance literature:

Multi-step reaction with 3 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

With n-butyllithium; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1002/hlca.19870700522

Reference yield:

methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate (104802-42-8) → (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 9 steps

1: 91 percent / DIBAH / CH₂Cl₂; toluene / 0.58 h / -70 °C

2: 77 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -118 °C

3: 89.4 percent / methanol / 0.5 h / Ambient temperature

4: 75 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -50 deg C, 15 min; 2.) room temp. 3 h

5: 97.5 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature

6: 96 percent / KOH/MeOH / 19 h / Ambient temperature

7: 71 percent / benzenesulfonyl chloride / pyridine / 22 h / 5 °C

8: 55 percent / pyridinium p-toluenesulfonate / ethanol / 2 h / 55 °C

9: 63.5 percent / 1.) DCC; 2.) p-(dimethylamino)pyridine / dimethylformamide / 0.5 h / Ambient temperature

With methanol; dmap; potassium hydroxide; n-butyllithium; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; benzenesulfonyl chloride; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1002/hlca.19870700522

Reference yield:

methyl (S,Z)-3-<(tetrahydro-2H-pyran-2-yl)oxy>-11-icosenoate (104802-42-8) → (R)-2-hydroxy-1,2,2-triphenylethyl (3S,5S,Z)-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>-13-docosenoate (114375-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / DIBAH / CH₂Cl₂; toluene / 0.58 h / -70 °C

2: 77 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -118 °C

With n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene;

DOI:10.1002/hlca.19870700522

upstream raw materials:

Oleic aldehyde

Downstream raw materials:

(R)-2-hydroxy-1,2,2-triphenylethyl (3S,5S,Z)-3-hydroxy-5-<(tetrahydro-2H-pyran-2-yl)oxy>-13-docosenoate