benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate

Base Information

• Chemical Name: benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate
• CAS No.: 1333964-81-0
• Molecular Formula: C₁₅H₁₈O₅
• Molecular Weight: 278.305
• Mol file: 1333964-81-0.mol

Synonyms:benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate

Chemical Property of benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate

Chemical Property:

Purity/Quality:

98.5% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate

There total 10 articles about benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate 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: 58.0%

trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol (862259-02-7) + benzyl alcohol (100-51-6,185532-71-2) → benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate (1333964-81-0)

Guidance literature:

With sodium carbonate; In toluene; for 6h; Inert atmosphere; Reflux;

Reference yield: 56.2%

3-Oxo-2-oxa-bicyclo[2.2.1]heptane-5-carboxylic acid methyl ester + benzyl alcohol (100-51-6,185532-71-2) → benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate (1333964-81-0)

Guidance literature:

With hydrogenchloride; In 1,4-dioxane; at 0 - 45 ℃; for 16h; Inert atmosphere;

Reference yield:

(1R,2R)-4-oxo-1,2-cyclopentanedicarboxylic acid bis-brucine salt → benzyl methyl (1R,2R,4R)-4-hydroxy-1,2-cyclopentanedicarboxylate (1333964-81-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: ammonium hydroxide / water / 0.5 h / 80 °C

1.2: 2 h / Reflux

2.1: hydrogen / 5 percent rhodium on alumina / tetrahydrofuran

3.1: sodium carbonate / toluene / 6 h / Inert atmosphere; Reflux

With ammonium hydroxide; hydrogen; sodium carbonate; 5 percent rhodium on alumina; In tetrahydrofuran; water; toluene;

upstream raw materials:

trans-(3R,4R)-3,4-bis(methoxycarbonyl)cyclopentanol

benzyl alcohol

racemic trans-cyclopentanone-3,4-dicarboxylic acid

(+)-(1S,2S)-dimethyl-4-oxocyclopentane 1,2-dicarboxylate

Downstream raw materials:

ethyl (1R,2S)-2-ethenyl-1-({[(1R,2R,4R)-2-[hex-5-en-1-yl-(methyl)carbamoyl]-4-({7-methoxy-8-methyl-2-[4-(propan-2-yl)-1,3-thiazol-2-yl]quinolin-4-yl}oxy)cyclopentyl]carbonyl}-amino)cyclopropanecarboxylate

methyl (1R,2R,4S)-2-[5-hexen-1-yl(methyl)carbamoyl]-4-[[2-(4-isopropyl-1,3-thiazol-2-yl)-7-methoxy-8-methyl-4-quinolinyl]oxy]cyclopentanecarboxylate

(1R,2R,4R)-2-(methoxycarbonyl)-4-[(4-nitrobenzoyl)oxy]cyclopentanecarboxylic acid

(1R,3R,4R)-3-[5-hexen-1-yl(methyl)-carbamoyl]-4-(methoxycarbonyl)cyclopentyl 4-nitrobenzoate