(4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester

Base Information

• Chemical Name: (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester
• CAS No.: 464173-89-5
• Molecular Formula: C₃₂H₄₂N₂O₈
• Molecular Weight: 582.694

Synonyms:(4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester

Chemical Property of (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester

There total 6 articles about (4R,5S)-N^α-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl 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: 96.0%

(4R,5S)-Nα-tert-butoxycarbonyl-5-[3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)allyl]-4-benzyl-L-proline ethyl ester (464173-88-4) → (4R,5S)-Nα-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester (464173-89-5)

Guidance literature:

With (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; hydrogen; In methanol; for 24h; under 3878.71 Torr;

DOI:10.1021/jo0203591

Reference yield:

ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate (153080-85-4) → (4R,5S)-Nα-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester (464173-89-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium triethylborohydride / tetrahydrofuran / 0.58 h / -78 °C

1.2: H₂O₂ / tetrahydrofuran; H₂O / 0.5 h / 0 °C

2.1: 4900 mg / (p-CH₃C₆H₄)SO₃H*H₂O / 20 °C

3.1: 76 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 °C

4.1: O₃ / CH₂Cl₂ / -78 °C

4.2: 63 percent / (CH₃)2S / CH₂Cl₂ / 120 h / 20 °C

5.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 20 °C

6.1: 96 percent / H₂; Rh(I)(1,5-COD)(1,2-bis{(S,S)-2,5-di-Et-(c-C₄H₈P)}C₆H₄)OTf / methanol / 24 h / 3878.71 Torr

With (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; lithium triethylborohydride; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; 5.1: Horner-Emmons olefination;

DOI:10.1021/jo0203591

Reference yield:

(2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester (750638-93-8) → (4R,5S)-Nα-tert-butoxycarbonyl-5-[(3S)-3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)propyl]-4-benzyl-L-proline ethyl ester (464173-89-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 4900 mg / (p-CH₃C₆H₄)SO₃H*H₂O / 20 °C

2.1: 76 percent / BF₃*Et₂O / diethyl ether / 3 h / -78 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: 63 percent / (CH₃)2S / CH₂Cl₂ / 120 h / 20 °C

4.1: 100 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 4 h / 20 °C

5.1: 96 percent / H₂; Rh(I)(1,5-COD)(1,2-bis{(S,S)-2,5-di-Et-(c-C₄H₈P)}C₆H₄)OTf / methanol / 24 h / 3878.71 Torr

With (+)-1,2-bis-((2S,5S)-2,5-diethylphospholano)benzene(cyclooctadiene)rhodium(I) trifluoromethanesulfonate; boron trifluoride diethyl etherate; hydrogen; toluene-4-sulfonic acid; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; diethyl ether; dichloromethane; 4.1: Horner-Emmons olefination;

DOI:10.1021/jo0203591

upstream raw materials:

(4R,5S)-N^α-tert-butoxycarbonyl-5-[3-(benzyloxycarbonyl)amino-3-(methoxycarbonyl)allyl]-4-benzyl-L-proline ethyl ester

ethyl (2S,4R)-1-(tert-butoxycarbonyl)-4-benzylpyroglutamate

(2S,4R)-4-Benzyl-5-hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester

(4R)-N^α-tert-butoxycarbonyl-4-benzyl-5-methoxy-L-proline ethyl ester

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