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

Base Information

• Chemical Name: 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
• CAS No.: 1359969-51-9
• Molecular Formula: C₂₉H₃₆N₆O₆
• Molecular Weight: 564.641

Synonyms: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

Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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: 50.0%

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) → 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 (1359969-51-9)

Guidance literature:

With lithium borohydride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere; Cooling with ice;

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) → 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 (1359969-51-9)

Guidance literature:

Multi-step reaction with 3 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

3.1: lithium borohydride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Cooling with ice

With lithium borohydride; 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 tetrahydrofuran; dichloromethane; 2.1: Huisgen cycloaddition / 2.2: Huisgen cycloaddition;

DOI:10.1021/ol3002199

Reference yield:

(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) → 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 (1359969-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.25 h / 20 °C / Inert atmosphere

1.2: 7 h / 20 °C / Inert atmosphere

2.1: lithium borohydride / tetrahydrofuran / 18 h / 20 °C / Inert atmosphere; Cooling with ice

With lithium borohydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane; 1.1: Huisgen cycloaddition / 1.2: 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

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