(3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester

Base Information

• Chemical Name: (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester
• CAS No.: 852714-87-5
• Molecular Formula: C₅₅H₇₄N₅O₈P
• Molecular Weight: 964.195
• Mol file: 852714-87-5.mol

Synonyms:(3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester

Chemical Property of (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester

There total 19 articles about (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl 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: 42.0%

2-{1-[4-(benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester (852714-86-4) + N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester (852714-87-5)

Guidance literature:

2-{1-[4-(benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester; With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In DMF (N,N-dimethyl-formamide); at 20 ℃; for 0.166667h;

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide; In DMF (N,N-dimethyl-formamide); at 20 - 45 ℃; for 31h;

Reference yield:

4-[4-(benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(2-oxo-4-phenyl-oxazolidine-3-carbonyl)-hex-5-enoic acid tert-butyl ester (852714-85-3) → (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester (852714-87-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

2: 320 mg / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

Reference yield:

Benzyl-{4-[(E)-3-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-propenyl]-benzyl}-phosphinic acid tert-butyl ester (852714-83-1) → (3S,4S)-4-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-3-(1-{(S)-2-carbamoyl-1-[(R)-2-(5-methyl-indol-1-ylmethyl)-pent-4-enylcarbamoyl]-ethylcarbamoyl}-cyclohexylcarbamoyl)-hex-5-enoic acid tert-butyl ester (852714-87-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: PhSCu / diethyl ether; tetrahydrofuran / -40 °C

1.2: 44 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

2.1: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

2.2: 480 mg / tetrahydrofuran / 1.5 h / -78 - 20 °C

3.1: 85 percent / aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

4.1: 320 mg / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

With lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; copper(I) thiophenolate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

upstream raw materials:

2-{1-[4-(benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester

N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide

Benzyl-{4-[(E)-3-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-propenyl]-benzyl}-phosphinic acid tert-butyl ester

Benzyl-(4-{(R)-1-[2-oxo-2-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-ethyl]-allyl}-benzyl)-phosphinic acid tert-butyl ester

Downstream raw materials:

[(E)-(9S,10S,14R,18S)-10-[4-(Benzyl-tert-butoxy-phosphinoylmethyl)-phenyl]-18-carbamoylmethyl-14-(5-methyl-indol-1-ylmethyl)-8,17,20-trioxo-7,16,19-triaza-spiro[5.14]icos-11-en-9-yl]-acetic acid tert-butyl ester