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)-3-methyl-5-triethylsilanyloxy-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)-3-methyl-5-triethylsilanyloxy-heptyl ester
• CAS No.: 582321-87-7
• Molecular Formula: C₅₁H₈₅N₅O₉SSi
• Molecular Weight: 972.415

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)-3-methyl-5-triethylsilanyloxy-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)-3-methyl-5-triethylsilanyloxy-heptyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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)-3-methyl-5-triethylsilanyloxy-heptyl ester

There total 26 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)-3-methyl-5-triethylsilanyloxy-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:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → 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)-3-methyl-5-triethylsilanyloxy-heptyl ester (582321-87-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisopropylethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C

1.2: 94 percent / N,N-dimethyl-4-aminopyridine / toluene / 3 h / 20 °C

2.1: 88 percent / tetra-N-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

3.1: 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

4.1: dicyclohexylboron chloride; Me₂NEt / diethyl ether / 1.5 h / 0 °C

4.2: diethyl ether / 19 h / -78 - -20 °C

4.3: aq. H₂O₂ / methanol / 3 h / 20 °C

5.1: 196 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -50 °C

6.1: K₂CO₃ / methanol / 2 h / 20 °C

7.1: 39.3 mg / aq. NaIO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

8.1: 75.5 mg / Et₃N; diphenylphosphoryl azide / dimethylformamide / 2 h / 20 °C

9.1: 93 percent / 2,6-dichloro-3,5-dicyanoquinone / CH₂Cl₂; aq. phosphate buffer / 1.5 h / 0 - 20 °C / pH 7

10.1: 97 percent / PPh₃; diisopropylazodicarboxylate; diphenylphosphorylazide / tetrahydrofuran / 0.33 h / 0 °C

11.1: HF-pyridine / tetrahydrofuran / 9 h / 20 °C

12.1: 17 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

13.1: 63 percent / PPh₃ / tetrahydrofuran / 12 h / 50 °C

14.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

15.1: 6.3 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

16.1: aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium periodate; tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; di-isopropyl azodicarboxylate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; diphenylphosphoranyl azide; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; 2,6-dichloro-3,5-dicyano-1,4-benzoquinone; potassium carbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 10.1: Mitsunobu reaction / 13.1: Staudinger-aza-Wittig reaction;

DOI:10.1021/ja036050w

Reference yield:

(3S)-2,2-dimethyl-5-hexen-3-ol (67760-86-5) → 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)-3-methyl-5-triethylsilanyloxy-heptyl ester (582321-87-7)

Guidance literature:

Multi-step reaction with 21 steps

1.1: 71 percent / Et₃N; N-methyl-2-chloropyridinium iodide / CH₂Cl₂ / 2.5 h / Heating

2.1: titanium tetra-isopropoxide / CH₂Cl₂ / 1 h / 40 °C

2.2: 97 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 3 h / Heating

3.1: CuCN / diethyl ether / -78 - 0 °C

3.2: 86 percent / diethyl ether / 1 h / -78 - -25 °C

4.1: 83 percent / LiAlH₄ / diethyl ether / 0.67 h / 0 °C

5.1: 86 percent / imidazole / CH₂Cl₂ / 0.5 h / 20 °C

6.1: diisopropylethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 3 h / 20 °C

6.2: 94 percent / N,N-dimethyl-4-aminopyridine / toluene / 3 h / 20 °C

7.1: 88 percent / tetra-N-butylammonium fluoride / tetrahydrofuran / 5 h / 20 °C

8.1: 4 Angstroem molecular sieves; N-methylmorpholine-N-oxide; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 0.5 h / 20 °C

9.1: dicyclohexylboron chloride; Me₂NEt / diethyl ether / 1.5 h / 0 °C

9.2: diethyl ether / 19 h / -78 - -20 °C

9.3: aq. H₂O₂ / methanol / 3 h / 20 °C

10.1: 196 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -50 °C

11.1: K₂CO₃ / methanol / 2 h / 20 °C

12.1: 39.3 mg / aq. NaIO₄ / 2-methyl-propan-2-ol / 12 h / 20 °C

13.1: 75.5 mg / Et₃N; diphenylphosphoryl azide / dimethylformamide / 2 h / 20 °C

14.1: 93 percent / 2,6-dichloro-3,5-dicyanoquinone / CH₂Cl₂; aq. phosphate buffer / 1.5 h / 0 - 20 °C / pH 7

15.1: 97 percent / PPh₃; diisopropylazodicarboxylate; diphenylphosphorylazide / tetrahydrofuran / 0.33 h / 0 °C

16.1: HF-pyridine / tetrahydrofuran / 9 h / 20 °C

17.1: 17 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

18.1: 63 percent / PPh₃ / tetrahydrofuran / 12 h / 50 °C

19.1: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

20.1: 6.3 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

21.1: aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 20 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; lithium hydroxide; sodium periodate; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; N,N-dimethyl-ethanamine; di-isopropyl azodicarboxylate; 4 A molecular sieve; 2,4,6-trichlorobenzoyl chloride; diphenylphosphoranyl azide; dicyclohexylboron chloride; tetrabutyl ammonium fluoride; 2-chloro-1-methyl-pyridinium iodide; 2,6-dichloro-3,5-dicyano-1,4-benzoquinone; potassium carbonate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 15.1: Mitsunobu reaction / 18.1: Staudinger-aza-Wittig reaction;

DOI:10.1021/ja036050w

Reference yield:

methyl (2E,4R)-2-methyl-4-hydroxy-5-(t-butyldimethylsilyl)oxypent-2-enoate (122520-65-4) → 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)-3-methyl-5-triethylsilanyloxy-heptyl ester (582321-87-7)

Guidance literature:

Multi-step reaction with 15 steps

1: 75 percent / trifluoromethanesulfonic acid / diethyl ether / 0.17 h / 20 °C

2: 83 percent / aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran / 12 h / 20 °C

3: 69.1 mg / diisopropylethylamine; PyAOP / dimethylformamide / 2 h / 20 °C

4: 98 percent / HF*pyridine / tetrahydrofuran / 0.5 h / 20 °C

5: 85 percent / PPh₃; diisopropylazodicarboxylate / tetrahydrofuran / 0.08 h / 0 °C

6: K₂CO₃ / CH₂Cl₂; methanol / 1 h / 0 °C

7: 75.5 mg / Et₃N; diphenylphosphoryl azide / dimethylformamide / 2 h / 20 °C

8: 93 percent / 2,6-dichloro-3,5-dicyanoquinone / CH₂Cl₂; aq. phosphate buffer / 1.5 h / 0 - 20 °C / pH 7

9: 97 percent / PPh₃; diisopropylazodicarboxylate; diphenylphosphorylazide / tetrahydrofuran / 0.33 h / 0 °C

10: HF-pyridine / tetrahydrofuran / 9 h / 20 °C

11: 17 mg / 2,6-lutidine / CH₂Cl₂ / 2 h / -78 °C

12: 63 percent / PPh₃ / tetrahydrofuran / 12 h / 50 °C

13: 2,6-lutidine / CH₂Cl₂ / 0.5 h / 20 °C

14: 6.3 mg / tetra-n-butylammonium fluoride / tetrahydrofuran / 0.17 h / 0 °C

15: aq. LiOH / 2-methyl-propan-2-ol; tetrahydrofuran / 5 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; trifluorormethanesulfonic acid; di-isopropyl azodicarboxylate; diphenylphosphoranyl azide; tetrabutyl ammonium fluoride; 2,6-dichloro-3,5-dicyano-1,4-benzoquinone; potassium carbonate; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; phosphate buffer; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol; 9: Mitsunobu reaction / 12: Staudinger-aza-Wittig reaction;

DOI:10.1021/ja036050w

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

(3S)-2,2-dimethyl-5-hexen-3-ol

methyl (2E,4R)-2-methyl-4-hydroxy-5-(t-butyldimethylsilyl)oxypent-2-enoate

(4R,6S)-6-tert-butyl-4-methyltetrahydro-2H-pyran-2-one

Downstream raw materials:

(-)-apratoxin A

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 582321-87-7 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)-3-methyl-5-triethylsilanyloxy-heptyl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send