pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester

Base Information

• Chemical Name: pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester
• CAS No.: 878626-86-9
• Molecular Formula: C₄₅H₇₁N₅O₉S
• Molecular Weight: 858.153

Synonyms:pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester

Chemical Property of pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester

Chemical Property:

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Technology Process of pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester

There total 39 articles about pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl 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:

C60H81N5O11S → pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester (878626-86-9)

Guidance literature:

With diethylamine; In acetonitrile; at 20 ℃; for 0.5h;

DOI:10.1021/ol052907d

Reference yield:

(E)-(S)-4-Amino-2-methyl-5-tritylsulfanyl-pent-2-enoic acid allyl ester → pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester (878626-86-9)

Guidance literature:

Multi-step reaction with 11 steps

1: 372 mg / iPr₂NEt; HATU / CH₂Cl₂ / 10 h / 20 °C

2: 95 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

3: 2,6-lutidine; TMDOTf / CH₂Cl₂ / 0.5 h / 20 °C

4: 359 mg / iPr₂NEt / CH₂Cl₂; tetrahydrofuran / 0.67 h / 0 °C

5: 84 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

6: PPh₃O; Tf₂O / CH₂Cl₂ / 0.5 h / 0 °C

7: 28.2 mg / aq. NH₄OAc; Zn / tetrahydrofuran / 20 °C

8: 95 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / 20 °C

9: 30.7 mg / iPr₂NEt; HATU / CH₂Cl₂ / 8 h / 20 °C

10: N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

11: Et₂NH / acetonitrile / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; trifluoromethylsulfonic anhydride; TMDOTf; ammonium acetate; tetrabutyl ammonium fluoride; diethylamine; N-ethyl-N,N-diisopropylamine; N-methylaniline; Triphenylphosphine oxide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ol052907d

Reference yield:

(2E)-(4S)-4-N-tert-butoxycarbonylamino-2-methyl-5-(triphenylmethylthio)-2-pentenoic acid allyl ester (878626-74-5) → pyrrolidine-2-carboxylic acid 1-tert-butyl-6-(4-{2-[1-({1-[(1-carboxy-2-methyl-butyl)-methyl-carbamoyl]-ethyl}-methyl-carbamoyl)-2-(4-methoxy-phenyl)-ethylcarbamoyl]-propenyl}-4,5-dihydro-thiazol-2-yl)-5-hydroxy-3-methyl-heptyl ester (878626-86-9)

Guidance literature:

Multi-step reaction with 12 steps

1: TMSOTf; 2,6-lutidine / CH₂Cl₂ / 3 h / 20 °C

2: 372 mg / iPr₂NEt; HATU / CH₂Cl₂ / 10 h / 20 °C

3: 95 percent / TBAF / tetrahydrofuran / 0.33 h / 0 °C

4: 2,6-lutidine; TMDOTf / CH₂Cl₂ / 0.5 h / 20 °C

5: 359 mg / iPr₂NEt / CH₂Cl₂; tetrahydrofuran / 0.67 h / 0 °C

6: 84 percent / pyridine; DMAP / CH₂Cl₂ / 1 h / 20 °C

7: PPh₃O; Tf₂O / CH₂Cl₂ / 0.5 h / 0 °C

8: 28.2 mg / aq. NH₄OAc; Zn / tetrahydrofuran / 20 °C

9: 95 percent / N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 0.67 h / 20 °C

10: 30.7 mg / iPr₂NEt; HATU / CH₂Cl₂ / 8 h / 20 °C

11: N-methylaniline / Pd(PPh₃)4 / tetrahydrofuran / 0.25 h / 20 °C

12: Et₂NH / acetonitrile / 0.5 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; TMDOTf; ammonium acetate; tetrabutyl ammonium fluoride; diethylamine; N-ethyl-N,N-diisopropylamine; N-methylaniline; Triphenylphosphine oxide; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1021/ol052907d

upstream raw materials:

(S)-5,5-dimethyl-4-(4-methoxybenzyloxy)-2-hexanone

(2S,3S)-allyl 2-(tert-butoxycarbonyl(methyl)amino)-3-methylpentanoate

(E)-(S)-5-(4-methoxybenzyloxy)-3,6,6-trimethyl-2-hepten-1-ol

acetic acid 1-[2-(4-methoxy-benzyloxy)-3,3-dimethyl-butyl]-1-methyl-allyl ester

Downstream raw materials:

(-)-apratoxin A

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