((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester

Base Information

• Chemical Name: ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester
• CAS No.: 122221-88-9
• Molecular Formula: C₁₆H₁₈O₄S
• Molecular Weight: 306.383
• Mol file: 122221-88-9.mol

Synonyms:((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester

Chemical Property of ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester

There total 6 articles about ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl 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:

cis-3a,4,7,7a-tetrahydroindan-2-one (25886-63-9) → ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester (122221-88-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) KMnO₄, NaIO₄, Na₂CO₃; / 1.) aq. acetone; 2.) MeOH

2: 86 percent / porcine liver esterase, 0.1 M phosphate buffer / acetone / 2.5 h / Ambient temperature

3: 1.) Et-N=C=N(CH₂)3N(CH₃)2*HCl-hydroxybenzotriazole; 2.)Et₃N / 1.) THF, 0 deg C to rt; 2.) THF

With porcine liver esterase; potassium permanganate; sodium periodate; phosphate buffer; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetone;

DOI:10.1246/cl.1989.239

Reference yield:

cis-2,2'-(cyclohex-4-ene-1,2-diyl)diacetic acid (25886-62-8) → ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester (122221-88-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 97 percent / HCl / methanol

2: 92 percent / NaH / dimethylsulfoxide

3: 96 percent / HMPA / H₂O / 175 °C

4: 1.) KMnO₄, NaIO₄, Na₂CO₃; / 1.) aq. acetone; 2.) MeOH

5: 86 percent / porcine liver esterase, 0.1 M phosphate buffer / acetone / 2.5 h / Ambient temperature

6: 1.) Et-N=C=N(CH₂)3N(CH₃)2*HCl-hydroxybenzotriazole; 2.)Et₃N / 1.) THF, 0 deg C to rt; 2.) THF

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; porcine liver esterase; potassium permanganate; sodium periodate; phosphate buffer; sodium hydride; sodium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In methanol; water; dimethyl sulfoxide; acetone;

DOI:10.1246/cl.1989.239

Reference yield:

cis-4-oxocyclopentane-1,2-diacetic acid bis(methyl ester) (70871-19-1) → ((1S,2R)-4-Oxo-2-phenylsulfanylcarbonylmethyl-cyclopentyl)-acetic acid methyl ester (122221-88-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 86 percent / porcine liver esterase, 0.1 M phosphate buffer / acetone / 2.5 h / Ambient temperature

2: 1.) Et-N=C=N(CH₂)3N(CH₃)2*HCl-hydroxybenzotriazole; 2.)Et₃N / 1.) THF, 0 deg C to rt; 2.) THF

With porcine liver esterase; phosphate buffer; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In acetone;

DOI:10.1246/cl.1989.239

upstream raw materials:

thiophenol

(-)-(1S-cis)-4-oxocyclopentane-1,2-diacetic acid monomethyl ester

cis-3a,4,7,7a-tetrahydroindan-2-one

cis-2,2'-(cyclohex-4-ene-1,2-diyl)diacetic acid

Downstream raw materials:

((7S,8R)-8-Phenylsulfanylcarbonylmethyl-1,4-dioxa-spiro[4.4]non-7-yl)-acetic acid methyl ester