(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Base Information

Chemical Name:(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid
CAS No.:1027981-43-6
Molecular Formula:C₁₆H₁₉NO₇S
Molecular Weight:369.395
Hs Code.:

Synonyms:(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

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Chemical Property of (2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

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Technology Process of (2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

There total 10 articles about (2S,3S,4R)-4-Acetyl-3-carboxymethyl-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:

: 861145-12-2
(2S,3S,4R,S_R)-[4-acetyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidin-3-yl]acetaldehyde

: 1027981-43-6
(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: With ruthenium trichloride; sodium periodate; In water; ethyl acetate; acetonitrile; at 30 ℃; for 22h;
DOI:10.1021/ol051003p

Reference yield:

: 861145-04-2
(2S,3S,S_R)-2-(4-methoxyphenyl)-4-methylene-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

: 1027981-43-6
(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: 9-BBN (dimer) / tetrahydrofuran / 2.25 h / 50 °C

1.2: 91 percent / aq. NaOH; aq. H₂O₂ / tetrahydrofuran / -20 - 20 °C

2.1: 91 percent / NaBr; TEMPO; NaOCl / NaHCO₃ / ethyl acetate; toluene; H₂O / 0 °C

3.1: 99 percent / tetrahydrofuran / 5 h / -78 °C

4.1: 86 percent / KOBu-t / tetrahydrofuran / 3 h / 0 °C

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

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

6.2: 0.16844 g / tetrahydrofuran; toluene / 0 - 20 °C

7.1: 87 percent / Dess-Martin periodinane / CH₂Cl₂ / 5 h / 20 °C

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

8.2: 91 percent / aq. KI / tetrahydrofuran

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

With ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; potassium tert-butylate; mercury(II) diacetate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; n-heptane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/ol051003p

Reference yield:

: 861145-05-3
(2S,3S,4R,S_R)-4-hydroxymethyl-2-(4-methoxyphenyl)-1-(toluene-4-sulfinyl)-pyrrolidine-3-carboxylic acid diphenylamide

: 1027981-43-6
(2S,3S,4R)-4-Acetyl-3-carboxymethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2-carboxylic acid

Guidance literature:: Multi-step reaction with 8 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

With ruthenium trichloride; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium periodate; potassium tert-butylate; mercury(II) diacetate; potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; sodium bromide; sodium hydrogencarbonate; In tetrahydrofuran; n-heptane; dichloromethane; water; ethyl acetate; toluene; acetonitrile;
DOI:10.1021/ol051003p