methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate

Base Information

• Chemical Name: methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate
• CAS No.: 249536-82-1
• Molecular Formula: C₁₀H₁₄O₄
• Molecular Weight: 198.219
• Mol file: 249536-82-1.mol

Synonyms:

Chemical Property of methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate

There total 1 articles about methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate 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:

vinyl acetate (108-05-4,9003-20-7) + (1S,2S)-2-Hydroxy-1-methyl-cyclopent-3-enecarboxylic acid methyl ester (249537-15-3) → methyl (1S,2S)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate (206755-01-3,249537-15-3) + methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate (249536-82-1) + methyl (1R,2R)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate (249537-15-3) + methyl (1R,2R)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate

Guidance literature:

With lipase Amano P; at 33 ℃; for 168h; Title compound not separated from byproducts; Enzymatic reaction;

DOI:10.1248/cpb.47.1256

Reference yield: 42.0%

methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate (249536-82-1) → methyl (1S,2S)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate (206755-01-3,249537-15-3) + methyl (1S,4S)-4-hydroxy-1-methyl-2-cyclopentenecarboxylate (206755-02-4,249537-10-8)

Guidance literature:

methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate; With dichloro bis(acetonitrile) palladium(II); p-benzoquinone; In tetrahydrofuran; Heating;

With methanol; potassium carbonate; at 20 ℃; for 1h;

DOI:10.1248/cpb.47.1256

Reference yield:

methyl (1S,2S)-2-acetoxy-1-methyl-3-cyclopentenecarboxylate (249536-82-1) → 9-[(1R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-4-methyl-cyclopent-2-enyl]-6-chloro-9H-purin-2-ylamine

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,4-benzoquinone; PdCl₂(MeCN)2 / tetrahydrofuran / Heating

1.2: 42 percent / K₂CO₃; MeOH / 1 h / 20 °C

2.1: pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 20 °C

3.1: LiAlH₄ / tetrahydrofuran / 0.5 h / 20 °C

4.1: imidazole / dimethylformamide / 2 h / 20 °C

5.1: pyridinium p-toluenesulfonate / methanol / 3 h / 20 °C

6.1: Ph₃P; diethyl azodicarboxylate / tetrahydrofuran / 14 h / 20 °C

With 1H-imidazole; dichloro bis(acetonitrile) palladium(II); lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; triphenylphosphine; p-benzoquinone; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Rearrangement / 1.2: methanolysis / 2.1: Addition / 3.1: Reduction / 4.1: Condensation / 5.1: deprotection / 6.1: Condensation;

DOI:10.1248/cpb.47.1256

upstream raw materials:

vinyl acetate

(1S,2S)-2-Hydroxy-1-methyl-cyclopent-3-enecarboxylic acid methyl ester

Downstream raw materials:

methyl (1S,2S)-2-hydroxy-1-methyl-3-cyclopentenecarboxylate

methyl (1S,4S)-4-hydroxy-1-methyl-2-cyclopentenecarboxylate

(1S,4S)-4-(tert-butyldiphenylsilyloxymethyl)-4-methyl-2-cyclopentenol

Refernces