(E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione

Base Information

• Chemical Name: (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione
• CAS No.: 1385068-16-5
• Molecular Formula: C₂₅H₃₁N₃O₄
• Molecular Weight: 437.539

Synonyms:(E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione

Chemical Property of (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione

Chemical Property:

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Technology Process of (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione

There total 8 articles about (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1⁽¹⁸⁾,8,14,16-tetraene-2,13-dione 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: 48.0%

C25H30N2O7S + benzylamine (100-46-9) → (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),8,14,16-tetraene-2,13-dione (1385068-16-5)

Guidance literature:

In ethanol; for 24h; Reflux;

DOI:10.1016/j.bmc.2012.05.039

Reference yield:

C18H24N2O5 → (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),8,14,16-tetraene-2,13-dione (1385068-16-5)

Guidance literature:

Multi-step reaction with 2 steps

1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 23 h / 20 °C

2: ethanol / 24 h / Reflux

With di(n-butyl)tin oxide; triethylamine; In ethanol; dichloromethane;

DOI:10.1016/j.bmc.2012.05.039

Reference yield:

C14H17NO3 → (E)-(S)-4-((R)-2-benzylamino-1-hydroxy-ethyl)-16-methyl-6-oxa-3,12-diaza-bicyclo[12.3.1]octadeca-1(18),8,14,16-tetraene-2,13-dione (1385068-16-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: lithium hydroxide / 1,4-dioxane; water / 1.17 h / 20 °C

1.2: 16 h / 20 °C

2.1: acetic acid / water / 1.75 h / 60 °C

3.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / Inert atmosphere; Reflux

4.1: di(n-butyl)tin oxide; triethylamine / dichloromethane / 23 h / 20 °C

5.1: ethanol / 24 h / Reflux

With Hoveyda-Grubbs catalyst second generation; di(n-butyl)tin oxide; acetic acid; triethylamine; lithium hydroxide; In 1,4-dioxane; ethanol; dichloromethane; water;

DOI:10.1016/j.bmc.2012.05.039

upstream raw materials:

benzylamine

(S)-4-((S)-2-(allyloxy)-1-azidoethyl)-2,2-dimethyl-1,3-dioxolane

(S)-2-(allyloxy)-1-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethanamine

3-(methoxycarbonyl)-5-methylbenzoic acid

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