(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate

Base Information

• Chemical Name: (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate
• CAS No.: 1453815-12-7
• Molecular Formula: C₃₇H₄₆N₂O₁₀
• Molecular Weight: 678.78
• Mol file: 1453815-12-7.mol

Synonyms:(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate

Chemical Property of (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl carbamate

There total 2 articles about (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-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: 65.0%

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-21-iodo-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4, 6,10,18-pentaen-9-yl carbamate (75747-28-3) + 4-acetylphenylboronic acid (149104-90-5) → (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate (1453815-12-7)

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; cesium fluoride; In 1,4-dioxane; at 40 ℃; for 16h; Inert atmosphere;

DOI:10.1039/c3cc43457e

Reference yield:

geldanmycin (30562-34-6) → (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-acetylphenyl)-13-hydroxy-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl carbamate (1453815-12-7)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; iodine

2: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; cesium fluoride / 1,4-dioxane / 16 h / 40 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; iodine; cesium fluoride; In 1,4-dioxane; 2: |Suzuki-Miyaura Coupling;

DOI:10.1016/j.tet.2021.131927

upstream raw materials:

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-13-hydroxy-21-iodo-8,14,19-trimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-azabicyclo[16.3.1]docosa-1⁽²¹⁾,4, 6,10,18-pentaen-9-yl carbamate

4-acetylphenylboronic acid

geldanmycin