2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid

Base Information

• Chemical Name: 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid
• CAS No.: 790664-82-3
• Molecular Formula: C₂₃H₃₀O₄
• Molecular Weight: 370.489
• Mol file: 790664-82-3.mol

Synonyms:

Chemical Property of 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid

There total 7 articles about 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic 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:

ethyl (2E,4S)-4-<(benzyl)oxy>-2-pentenoate (113034-36-9) → 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid (790664-82-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / DIBAL-H / toluene; CH₂Cl₂ / 0.5 h / -20 °C

2.1: 71 percent / (-)-diisopropyl tartrate; titanium isopropoxide; cumene hydroperoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

3.1: copper(I) iodide / diethyl ether; hexane / 0.5 h / -20 °C

3.2: 80 percent / diethyl ether; hexane / 1 h / -20 °C

4.1: 83 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

5.1: NaH / dimethylformamide / 0.25 h / 0 °C

5.2: 85 percent / dimethylformamide / 0.5 h / 20 °C

6.1: 80 percent / PTSA / methanol / 0.5 h / 20 °C

7.1: 89 percent / pyridinium chlorochromate; NaOAc / CH₂Cl₂ / 0.75 h / 20 °C

8.1: 85 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 6 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium chlorite; copper(l) iodide; (-)-diisopropyl tartrate; Cumene hydroperoxide; dihydrogen peroxide; sodium acetate; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; 4 A molecular sieve; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 2.1: Sharpless asymmetric epoxidation;

DOI:10.1055/s-2004-829173

Reference yield:

(2E,4S)-4-<(benzyl)oxy>-2-pentenol (119242-59-0) → 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid (790664-82-3)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 71 percent / (-)-diisopropyl tartrate; titanium isopropoxide; cumene hydroperoxide / 4 Angstroem molecular sieves / CH₂Cl₂ / 12 h / -20 °C

2.1: copper(I) iodide / diethyl ether; hexane / 0.5 h / -20 °C

2.2: 80 percent / diethyl ether; hexane / 1 h / -20 °C

3.1: 83 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

4.1: NaH / dimethylformamide / 0.25 h / 0 °C

4.2: 85 percent / dimethylformamide / 0.5 h / 20 °C

5.1: 80 percent / PTSA / methanol / 0.5 h / 20 °C

6.1: 89 percent / pyridinium chlorochromate; NaOAc / CH₂Cl₂ / 0.75 h / 20 °C

7.1: 85 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 6 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; sodium chlorite; copper(l) iodide; (-)-diisopropyl tartrate; Cumene hydroperoxide; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; 4 A molecular sieve; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 1.1: Sharpless asymmetric epoxidation;

DOI:10.1055/s-2004-829173

Reference yield:

3-[1-benzyloxy-(1R)-ethyl]-(2R)-oxiran-2-yl methanol (553663-81-3) → 2-[1,2-di(benzyloxy)-(1S,2S)-propyl]-(2R)-hexanoic acid (790664-82-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: copper(I) iodide / diethyl ether; hexane / 0.5 h / -20 °C

1.2: 80 percent / diethyl ether; hexane / 1 h / -20 °C

2.1: 83 percent / imidazole / CH₂Cl₂ / 1 h / 20 °C

3.1: NaH / dimethylformamide / 0.25 h / 0 °C

3.2: 85 percent / dimethylformamide / 0.5 h / 20 °C

4.1: 80 percent / PTSA / methanol / 0.5 h / 20 °C

5.1: 89 percent / pyridinium chlorochromate; NaOAc / CH₂Cl₂ / 0.75 h / 20 °C

6.1: 85 percent / NaClO₂; aq. H₂O₂ / 2-methyl-propan-2-ol / 6 h / 20 °C

With 1H-imidazole; sodium chlorite; copper(l) iodide; dihydrogen peroxide; sodium acetate; sodium hydride; toluene-4-sulfonic acid; pyridinium chlorochromate; In methanol; diethyl ether; hexane; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1055/s-2004-829173

upstream raw materials:

ethyl (2E,4S)-4-<(benzyl)oxy>-2-pentenoate

(2E,4S)-4-<(benzyl)oxy>-2-pentenol

3-[1-benzyloxy-(1R)-ethyl]-(2R)-oxiran-2-yl methanol

4-benzyloxy-2-butyl-(2S,3S,4S)-pentane-1,3-diol