Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester

Base Information

• Chemical Name: Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester
• CAS No.: 357274-61-4
• Molecular Formula: C₁₅H₁₈O₃
• Molecular Weight: 246.306
• Mol file: 357274-61-4.mol

Synonyms:Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester

Chemical Property of Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester

There total 3 articles about Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester 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: 87.0%

benzyl bromide (100-39-0) + Acetic acid (1R,4S,5R)-4-hydroxy-5-methyl-cyclopent-2-enyl ester (357274-60-3) → Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester (357274-61-4)

Guidance literature:

With potassium iodide; silver(l) oxide; In toluene; at 20 ℃; for 15.5h;

DOI:10.1016/S0040-4039(01)00649-9

Reference yield:

methylcyclopentadiene (96-38-8) → Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester (357274-61-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: O₂; rose bengal; AcONa / methanol / 1.33 h / -78 °C

1.2: 35 percent / (NH₂)2CS / methanol / 13 h / 20 °C

2.1: 94 percent / lipase AK / tetrahydrofuran / 7 h / 20 °C

3.1: 87 percent / Ag₂O; KI / toluene / 15.5 h / 20 °C

With lipase AK; oxygen; sodium acetate; rose bengal; potassium iodide; silver(l) oxide; In tetrahydrofuran; methanol; toluene;

DOI:10.1016/S0040-4039(01)00649-9

Reference yield:

(1R,2R,3S)-2-Methyl-cyclopent-4-ene-1,3-diol (357274-57-8) → Acetic acid (1R,4S,5R)-4-benzyloxy-5-methyl-cyclopent-2-enyl ester (357274-61-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 94 percent / lipase AK / tetrahydrofuran / 7 h / 20 °C

2: 87 percent / Ag₂O; KI / toluene / 15.5 h / 20 °C

With lipase AK; potassium iodide; silver(l) oxide; In tetrahydrofuran; toluene;

DOI:10.1016/S0040-4039(01)00649-9

upstream raw materials:

benzyl bromide

Acetic acid (1R,4S,5R)-4-hydroxy-5-methyl-cyclopent-2-enyl ester

methylcyclopentadiene

(1R,2R,3S)-2-Methyl-cyclopent-4-ene-1,3-diol

Downstream raw materials:

(S)-2-((2R,3S,4R)-2,4-Bis-benzyloxy-3-methyl-pentanoylamino)-3-hydroxy-2-methyl-propionic acid benzyl ester

(3R,4S,5S)-3-Benzyloxy-5-hydroxymethyl-4-methyl-dihydro-furan-2-one

(2R,3S,4R)-2,4-dibenzyloxy-3-methylpentanoic acid

methyl (2R,3S,4R)-2-(benzyloxy)-4-hydroxy-3-methylpentanoate