benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-yl]carbamate

Base Information

• Chemical Name: benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-yl]carbamate
• CAS No.: 1359969-05-3
• Molecular Formula: C₃₂H₄₀N₆O₆
• Molecular Weight: 604.706

Synonyms:benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-yl]carbamate

Chemical Property of benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-yl]carbamate

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Technology Process of benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-yl]carbamate

There total 12 articles about benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-12-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: 80.0%

benzyl N-[(12S,15S,18S)-18-(hydroxymethyl)-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-12-yl]carbamate (1359969-89-3) → benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-12-yl]carbamate (1359969-05-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1.25h; Inert atmosphere;

DOI:10.1021/ol3002199

Reference yield: 80.0%

→ benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-12-yl]carbamate (1359969-05-3)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

Reference yield:

(S)-6-azido-2-(benzyloxycarbonylamino)hexanoic acid → benzyl N-[(12S,15S,18S)-18-formyl-15-(2-methylpropyl)-13,16-dioxo-2-oxa-5,6,7,14,17-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-12-yl]carbamate (1359969-05-3)

Guidance literature:

Multi-step reaction with 5 steps

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

2.1: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere

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

5.1: Dess-Martin periodane / dichloromethane / 1.25 h / 20 °C / Inert atmosphere

With benzotriazol-1-ol; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; 4.1: Huisgen cycloaddition / 4.2: Huisgen cycloaddition;

DOI:10.1021/ol3002199

upstream raw materials:

(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl) propanoate

C₁₃H₁₅NO₃

(S)-2-amino-3-(4-(prop-2-yn-1-yloxy)phenyl)propan-1-ol

(S)-tert-butyl 2-((S)-6-azido-2-(((benzyloxy)carbonyl)amino)hexanamido)-4-methylpentanoate

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