(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester

Base Information

• Chemical Name: (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester
• CAS No.: 162362-11-0
• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.328

Synonyms:(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester

Chemical Property of (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester

Chemical Property:

Purity/Quality:

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Technology Process of (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester

There total 4 articles about (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) 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: 91.0%

(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-((S)-1-phenyl-ethyl) ester (162361-96-8) → (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester (162362-11-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00093a013

Reference yield:

(S)-1-phenylethanol (1445-91-6) → (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester (162362-11-0)

Guidance literature:

Multi-step reaction with 4 steps

1: toluene / Heating

2: conc. H₂SO₄ / CH₂Cl₂ / Ambient temperature

3: BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

4: 91 percent / CF₃CO₂H / CH₂Cl₂ / 24 h / Ambient temperature

With sulfuric acid; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane; toluene;

DOI:10.1021/ja00093a013

Reference yield:

(Z)-But-2-enedioic acid mono-((S)-1-phenyl-ethyl) ester (165304-73-4) → (1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid mono-((S)-1-phenyl-ethyl) ester (162362-11-0)

Guidance literature:

Multi-step reaction with 3 steps

1: conc. H₂SO₄ / CH₂Cl₂ / Ambient temperature

2: BF₃*OEt₂ / CH₂Cl₂ / 1 h / -78 °C

3: 91 percent / CF₃CO₂H / CH₂Cl₂ / 24 h / Ambient temperature

With sulfuric acid; boron trifluoride diethyl etherate; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/ja00093a013

upstream raw materials:

(1S,2R,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-((S)-1-phenyl-ethyl) ester

(S)-1-phenylethanol

(Z)-But-2-enedioic acid mono-((S)-1-phenyl-ethyl) ester

tert-butyl (S)-α-phenethyl maleate

Downstream raw materials:

(+)-2-endo-3-exo-Bis(hydroxymethyl)-bicyclo<2.2.1>hept-5-ene

(1S,2S,3S,4R)-Bicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid 2-tert-butyl ester 3-((S)-1-phenyl-ethyl) ester

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