methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate

Base Information

• Chemical Name: methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate
• CAS No.: 1359969-45-1
• Molecular Formula: C₃₀H₃₆N₆O₇
• Molecular Weight: 592.652
• Mol file: 1359969-45-1.mol

Synonyms:methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate

Chemical Property of methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate

There total 5 articles about methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaene-9-carboxylate 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: 65.0%

(5S,8S,11S)-methyl 11-(azidomethyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-5-(4-(prop-2-yn-1-yloxy)benzyl)-2-oxa-4,7,10-triazadodecan-12-oate (1359969-39-3) → methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1(19),4(22),5,17,20-pentaene-9-carboxylate (1359969-45-1)

Guidance literature:

(5S,8S,11S)-methyl 11-(azidomethyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-5-(4-(prop-2-yn-1-yloxy)benzyl)-2-oxa-4,7,10-triazadodecan-12-oate; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 20 ℃; for 0.25h; Inert atmosphere;

With copper(I) bromide; In dichloromethane; at 20 ℃; for 7h; Inert atmosphere;

DOI:10.1021/ol3002199

Reference yield:

(S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoic acid (1359969-36-0) → methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1(19),4(22),5,17,20-pentaene-9-carboxylate (1359969-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

2.2: 7 h / 20 °C / Inert atmosphere

With benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; 2.1: Huisgen cycloaddition / 2.2: Huisgen cycloaddition;

DOI:10.1021/ol3002199

Reference yield:

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanoic acid (1359969-23-5) → methyl (9S,12S,15S)-15-{[(benzyloxy)carbonyl]amino}-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1(19),4(22),5,17,20-pentaene-9-carboxylate (1359969-45-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

2.1: lithium hydroxide / tetrahydrofuran; water / 16 h / 0 - 20 °C

2.2: pH 7

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C

4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

4.2: 7 h / 20 °C / Inert atmosphere

With benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; 4.1: Huisgen cycloaddition / 4.2: Huisgen cycloaddition;

DOI:10.1021/ol3002199

upstream raw materials:

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanoic acid

(S)-methyl 2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoate

(S)-2-((S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanamido)-4-methylpentanoic acid

(5S,8S,11S)-methyl 11-(azidomethyl)-8-isobutyl-3,6,9-trioxo-1-phenyl-5-(4-(prop-2-yn-1-yloxy)benzyl)-2-oxa-4,7,10-triazadodecan-12-oate

Downstream raw materials:

benzyl N-[(9S,12S,15S)-9-formyl-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaen-15-yl]carbamate

benzyl N-[(9S,12S,15S)-9-(hydroxymethyl)-12-(2-methylpropyl)-11,14-dioxo-2-oxa-5,6,7,10,13-pentaazatricyclo[15.2.2.1(4,7)]docosa-1⁽¹⁹⁾,4⁽²²⁾,5,17,20-pentaen-15-yl]carbamate