(2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid
• CAS No.: 301832-55-3
• Molecular Formula: C₁₇H₂₁NO₆S
• Molecular Weight: 367.423
• Mol file: 301832-55-3.mol

Synonyms:(2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Chemical Property of (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

There total 42 articles about (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid 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:

(2S,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (150674-68-3) → (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (301832-55-3)

Guidance literature:

With lithium hydroxide; In methanol;

DOI:10.1016/S0040-4020(00)00579-2

Reference yield:

methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate (150674-69-4) → (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (301832-55-3)

Guidance literature:

With lithium hydroxide; In methanol; water; Ambient temperature;

DOI:10.1016/S0040-4039(00)79176-3

Reference yield:

(2S,3S,4R,SR)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide (861145-05-3) → (2S,3S,4S)-3-Carboxymethyl-4-isopropenyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid (301832-55-3)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 91 percent / NaBr; TEMPO; NaOCl / NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

2.1: 99 percent / tetrahydrofuran / 5 h / -78 °C

3.1: 86 percent / KOBu-t / tetrahydrofuran / 3 h / 0 °C

4.1: DIBAL-H / tetrahydrofuran; heptane / 4.5 h / -78 °C

5.1: KHMDS / tetrahydrofuran; toluene / 1 h / -78 - 0 °C

5.2: 0.16844 g / tetrahydrofuran; toluene / 0 - 20 °C

6.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

7.1: Hg(OAc)2 / tetrahydrofuran / -10 - 20 °C

7.2: 91 percent / aq. KI / tetrahydrofuran

8.1: NaIO₄; RuCl₃ / ethyl acetate; acetonitrile; H₂O / 22 h / 30 °C

9.1: 0.11704 g / diethyl ether / 0.17 h

10.1: 71 percent / Zn TiCl₄ / tetrahydrofuran / 0.25 h / 25 °C

11.1: aq. LiOH / methanol / 1 h / Heating

With ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; sodium periodate; potassium tert-butylate; mercury(II) diacetate; titanium tetrachloride; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; sodium bromide; zinc; sodium hydrogencarbonate; In tetrahydrofuran; methanol; diethyl ether; n-heptane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;

DOI:10.1021/ol051003p

upstream raw materials:

methyl [2S-(2α,3β,4β)]-[2-(methoxycarbonyl)-4-(1-methylethenyl)-1-(4-methylphenyl)sulfonyl]-3-pyrrolidineacetate

(2S,3S,4S)-4-Isopropenyl-3-methoxycarbonylmethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

(6S,3aR,6aS,S_R)-6-(4-methoxyphenyl)-3-methyl-5-(toluene-4-sulfinyl)-hexahydro-furo[3,4-c]pyrrol-1-one

(2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde

Downstream raw materials:

(-)-kainic acid