ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate

Base Information

• Chemical Name: ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate
• CAS No.: 291517-59-4
• Molecular Formula: C₂₅H₃₆N₂O₈
• Molecular Weight: 492.569
• Mol file: 291517-59-4.mol

Synonyms:ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate

Chemical Property of ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate

There total 6 articles about ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate 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: 56.0%

ethyl (2S)-cis-(Z)-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-2'-propenyl]prolinate → ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate (291517-59-4) + ethyl (2S,3'R)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate (291517-60-7)

Guidance literature:

With hydrogen; platinum on activated charcoal; In ethyl acetate; at 22 ℃; for 96h; under 2250.18 Torr;

DOI:10.1016/S0040-4020(00)00355-0

Reference yield:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate (144978-35-8,144978-12-1,251924-83-1) → ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate (291517-59-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 91 percent / DIBAL / tetrahydrofuran / 0.5 h / -78 °C

2.1: 80 percent / PPTS / 0.5 h / 22 °C

3.1: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / -90 °C

4.1: 91 percent / methanol; CH₂Cl₂ / -78 °C

5.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

5.2: 67 percent / CH₂Cl₂ / 1.5 h / -78 °C

6.1: 56 percent / H₂ / Pt/C / ethyl acetate / 96 h / 22 °C / 2250.18 Torr

With boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; platinum on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1.1: Reduction / 2.1: Etherification / 3.1: allylation / 4.1: ozonolysis / 5.1: Metallation / 5.2: Condensation / 6.1: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(00)00355-0

Reference yield:

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (194594-23-5) → ethyl (2S,3'S)-cis-1-(tert-butyloxycarbonyl)-5-[(3'-amino-(N-benzyloxycarbonyl)-3'-methoxycarbonyl)-propyl]prolinate (291517-59-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 80 percent / PPTS / 0.5 h / 22 °C

2.1: 79 percent / BF₃*OEt₂ / CH₂Cl₂ / -90 °C

3.1: 91 percent / methanol; CH₂Cl₂ / -78 °C

4.1: KOtBu / CH₂Cl₂ / 1 h / -78 °C

4.2: 67 percent / CH₂Cl₂ / 1.5 h / -78 °C

5.1: 56 percent / H₂ / Pt/C / ethyl acetate / 96 h / 22 °C / 2250.18 Torr

With boron trifluoride diethyl etherate; potassium tert-butylate; hydrogen; pyridinium p-toluenesulfonate; platinum on activated charcoal; In methanol; dichloromethane; ethyl acetate; 1.1: Etherification / 2.1: allylation / 3.1: ozonolysis / 4.1: Metallation / 4.2: Condensation / 5.1: Catalytic hydrogenation;

DOI:10.1016/S0040-4020(00)00355-0

upstream raw materials:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

ethyl (2S,5R/S)-1-(tert-butyloxycarbonyl)-5-(formylmethyl)prolinate

(2S,5R/S)-1-(tert-butyloxycarbonyl-5-ethoxy)-proline ethyl ester