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

Base Information

• Chemical Name: benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-18-yl]carbamate
• CAS No.: 1359968-98-1
• Molecular Formula: C₃₂H₄₀N₆O₆
• Molecular Weight: 604.706

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

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

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

There total 14 articles about benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1⁽²²⁾,4⁽²⁵⁾,5,20,23-pentaen-18-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)-12-(hydroxymethyl)-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-18-yl]carbamate (1359969-54-2) → benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-18-yl]carbamate (1359968-98-1)

Guidance literature:

With Dess-Martin periodane; In dichloromethane;

DOI:10.1002/chem.201204260

Reference yield:

(S)-2-(((benzyloxy)carbonyl)amino)-3-(4-(prop-2-yn-1-yloxy)phenyl)propanoic acid (1359969-23-5) → benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-18-yl]carbamate (1359968-98-1)

Guidance literature:

Multi-step reaction with 6 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

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

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

With lithium borohydride; 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; lithium hydroxide; In tetrahydrofuran; dichloromethane; water; 4.1: Huisgen cycloaddition / 4.2: Huisgen cycloaddition;

DOI:10.1021/ol3002199

Reference yield:

methyl (12S,15S,18S)-18-{[(benzyloxy)carbonyl]amino}-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaene-12-carboxylate (1359969-48-4) → benzyl N-[(12S,15S,18S)-12-formyl-15-(2-methylpropyl)-14,17-dioxo-2-oxa-5,6,7,13,16-pentaazatricyclo[18.2.2.1(4,7)]pentacosa-1(22),4(25),5,20,23-pentaen-18-yl]carbamate (1359968-98-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With lithium borohydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

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-amino-6-azidohexanoate hydrochloride

(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

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