dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate

Base Information

• Chemical Name: dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate
• CAS No.: 102607-65-8
• Molecular Formula: C₂₀H₂₀O₈
• Molecular Weight: 388.374

Synonyms:dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate

Chemical Property of dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate

Chemical Property:

Purity/Quality:

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Technology Process of dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate

There total 7 articles about dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate 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: 95.0%

methyl 3,4-dihydroxycinnamate (3843-74-1,67667-67-8) → dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate (102607-65-8)

Guidance literature:

In water; at 20 ℃; for 18h; stereospecific reaction; Irradiation;

DOI:10.1039/d0ce01403f

Reference yield:

caffeic acid (331-39-5,501-16-6) → dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate (102607-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dicyclohexyl-carbodiimide; dmap / methanol / 16 h / Reflux

2: water / 18 h / 20 °C / Irradiation

With dmap; dicyclohexyl-carbodiimide; In methanol; water; 1: |Steglich Esterification;

DOI:10.1039/d0ce01403f

Reference yield:

2,4-bis-(4-hydroxy-3-methoxy-phenyl)-cyclobutane-1,3-dicarboxylic acid dimethyl ester → dimethyl rel-(1R,2R,3S,4S)-2,4-bis(3,4-dihydroxyphenyl)cyclobutane-1,3-dicarboxylate (102607-65-8)

Guidance literature:

With pyridine; aluminium trichloride; In dichloromethane; Heating;

DOI:10.1016/j.tetlet.2004.11.042

upstream raw materials:

2,4-bis(3-methoxy-4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)-1,3-cyclobutanedicarboxylic acid

α-2,4-di(4-hydroxy-3-methoxyphenyl)cyclobutane-1,3-dicarboxylic acid

n-butyl caffeate

caffeic acid

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