(3S,4S)-4-[4-(tert-Butoxy-methyl-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-(tert-Butoxy-methyl-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.: 852714-95-5
• Molecular Formula: C₄₉H₇₀N₅O₈P
• Molecular Weight: 888.097
• Mol file: 852714-95-5.mol

Synonyms:(3S,4S)-4-[4-(tert-Butoxy-methyl-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-(tert-Butoxy-methyl-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-(tert-Butoxy-methyl-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 18 articles about (3S,4S)-4-[4-(tert-Butoxy-methyl-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:

C15H19O6P + N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → (3S,4S)-4-[4-(tert-Butoxy-methyl-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 (852714-95-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1,3-di-tert-butylcarbodiimide; In DMF (N,N-dimethyl-formamide); at 20 - 40 ℃; for 20.5h;

Reference yield:

2-{1-[4-(tert-butoxy-methyl-phosphinoylmethyl)-phenyl]-allyl}-succinic acid 4-tert-butyl ester (857083-13-7) + N-{(2R)-2-[(5-methylindol-1-yl)methyl]pent-4-enyl}(2S)-2-[(aminocyclohexyl)carbonylamino]-3-carbamoylpropanamide (666259-67-2) → (3S,4S)-4-[4-(tert-Butoxy-methyl-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 (852714-95-5)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 - 50 ℃; for 72h;

DOI:10.1021/jm050059m

Reference yield:

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one (852714-90-0) → (3S,4S)-4-[4-(tert-Butoxy-methyl-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 (852714-95-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 73 percent / tri-O-tolylphosphine; Pd(OAc)2; Et₃N / 12 h / Heating

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

2.2: 76 percent / diethyl ether; tetrahydrofuran / 1.1 h / -40 °C

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

3.2: 61 percent / tetrahydrofuran / 1.5 h / -78 - 20 °C

4.1: TFA / CH₂Cl₂ / 1.5 h / 0 °C

5.1: aq. H₂O₂; LiOH / tetrahydrofuran / 5 h / 20 °C

6.1: 240 mg / HOAt; EDCI*HCl / dimethylformamide / 72 h / 20 - 50 °C

With palladium diacetate; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; dihydrogen peroxide; copper(I) thiophenolate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; tris-(o-tolyl)phosphine; trifluoroacetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm050059m

upstream raw materials:

2-{1-[4-(tert-butoxy-methyl-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

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one

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

Downstream raw materials:

[(E)-(9S,10S,14R,18S)-10-[4-(tert-Butoxy-methyl-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