(R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate

Base Information

• Chemical Name: (R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate
• CAS No.: 104802-41-7
• Molecular Formula: C₄₀H₅₄O₄
• Molecular Weight: 598.866
• Mol file: 104802-41-7.mol

Synonyms:(R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate

Chemical Property of (R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate

There total 1 articles about (R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-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: 71.0%

Oleic aldehyde (2423-10-1) + (R)-2-acetoxy-1,1,2-triphenylethanol (95061-47-5) → (R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate (104802-41-7)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; diethyl ether; at -112 ℃; for 1h;

DOI:10.1002/hlca.19870700522

Reference yield:

(R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate (104802-41-7) → (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 11 steps

1: methanol / 1 h / Ambient temperature

2: 74.5 percent / TsOH / CH₂Cl₂ / 0.75 h / 0 °C

3: 91 percent / DIBAH / CH₂Cl₂; toluene / 0.58 h / -70 °C

4: 77 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -118 °C

5: 89.4 percent / methanol / 0.5 h / Ambient temperature

6: 75 percent / BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.) -50 deg C, 15 min; 2.) room temp. 3 h

7: 97.5 percent / hydrogen / Pd/C (10percent) / tetrahydrofuran / Ambient temperature

8: 96 percent / KOH/MeOH / 19 h / Ambient temperature

9: 71 percent / benzenesulfonyl chloride / pyridine / 22 h / 5 °C

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

11: 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; toluene-4-sulfonic acid; 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:

(R)-2-hydroxy-1,2,2-triphenylethyl (S,Z)-3-hydroxy-11-icosenoate (104802-41-7) → (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 4 steps

1: methanol / 1 h / Ambient temperature

2: 74.5 percent / TsOH / CH₂Cl₂ / 0.75 h / 0 °C

3: 91 percent / DIBAH / CH₂Cl₂; toluene / 0.58 h / -70 °C

4: 77 percent / BuLi / tetrahydrofuran; diethyl ether / 1 h / -118 °C

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

DOI:10.1002/hlca.19870700522

upstream raw materials:

Oleic aldehyde

(R)-2-acetoxy-1,1,2-triphenylethanol

Downstream raw materials:

(R)-1,1,2-triphenylethane-1,2-diol

methyl (Z,S)-3-hydroxy-11-icosenoate

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