Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester
• CAS No.: 202335-52-2
• Molecular Formula: C₁₇H₂₄O₃S
• Molecular Weight: 308.442
• Mol file: 202335-52-2.mol

Synonyms:Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester

Chemical Property of Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester

There total 10 articles about Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-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:

norborn-5-en-2-one (694-98-4) → Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester (202335-52-2)

Guidance literature:

Multi-step reaction with 9 steps

1: NaBH₄ / methanol / -10 °C

2: DMAP, pyridine / Ambient temperature

4: 88 percent / LiAlH₄ / diethyl ether / 1.) -5 deg C, 2 h, 2.) 0 deg C, 1 h

5: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, from -50 to 10 deg C, 2.) CH₂Cl₂, from -30 deg C to RT

6: 1.) H₂SO₄, 30percent aq. H₂O₂, 2.) sodium sulfite / 1.) ether

7: 1.) CuBr, Me₂S / 1.) THF, 15 min, 2.) THF, 0.5 h

8: LiAlH₄ / diethyl ether / 1.) -5 deg C, 2 h, 2.) 0 deg C, 1 h

9: DMAP, DCM, pyridine

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide; sulfuric acid; dihydrogen peroxide; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; dimethyl sulfoxide; triethylamine; copper(I) bromide; sodium sulfite; In methanol; diethyl ether;

DOI:10.1016/S0968-0896(97)00162-4

Reference yield:

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one (56487-70-8) → Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester (202335-52-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) CuBr, Me₂S / 1.) THF, 15 min, 2.) THF, 0.5 h

2: LiAlH₄ / diethyl ether / 1.) -5 deg C, 2 h, 2.) 0 deg C, 1 h

3: DMAP, DCM, pyridine

With pyridine; dmap; lithium aluminium tetrahydride; dimethylsulfide; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; copper(I) bromide; In diethyl ether;

DOI:10.1016/S0968-0896(97)00162-4

Reference yield:

(1S,2S,4S)-bicyclo[2.2.1]hept-5-en-2-ol (694-97-3,2890-98-4,13080-90-5,69769-90-0,71030-14-3,71030-15-4,87392-59-4,106928-44-3,16620-80-7) → Toluene-4-sulfonic acid 2-((1S,4R)-4-propyl-cyclopent-2-enyl)-ethyl ester (202335-52-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, from -50 to 10 deg C, 2.) CH₂Cl₂, from -30 deg C to RT

2: 1.) H₂SO₄, 30percent aq. H₂O₂, 2.) sodium sulfite / 1.) ether

3: 1.) CuBr, Me₂S / 1.) THF, 15 min, 2.) THF, 0.5 h

4: LiAlH₄ / diethyl ether / 1.) -5 deg C, 2 h, 2.) 0 deg C, 1 h

5: DMAP, DCM, pyridine

With pyridine; dmap; lithium aluminium tetrahydride; oxalyl dichloride; dimethylsulfide; sulfuric acid; dihydrogen peroxide; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; dimethyl sulfoxide; triethylamine; copper(I) bromide; sodium sulfite; In diethyl ether;

DOI:10.1016/S0968-0896(97)00162-4

upstream raw materials:

p-toluenesulfonyl chloride

2-((1S,4R)-4-Propyl-cyclopent-2-enyl)-ethanol

(3aS,6aR)-3,3a,4,6a-tetrahydro-2H-cyclopenta[b]furan-2-one

norborn-5-en-2-one