[(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

Base Information

• Chemical Name: [(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
• CAS No.: 852714-96-6
• Molecular Formula: C₄₇H₆₆N₅O₈P
• Molecular Weight: 860.043
• Mol file: 852714-96-6.mol

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 9 articles about [(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 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: 100.0%

→ [(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 (852714-96-6)

Guidance literature:

Reference yield:

(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) → [(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 (852714-96-6)

Guidance literature:

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 65 ℃; for 24h;

DOI:10.1021/jm050059m

Reference yield:

(tert-butoxy)[(4-bromophenyl)methyl]methylphosphin-1-one (852714-90-0) → [(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 (852714-96-6)

Guidance literature:

Multi-step reaction with 7 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

7.1: [((PCy₃)(Im(Mes)2)Ru=CHPh)]Cl₂ / CH₂Cl₂ / 24 h / 65 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 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:

(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

(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

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