(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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.: 1427297-08-2
• Molecular Formula: C₃₈H₅₁FN₄O₈
• Molecular Weight: 710.843

Synonyms:(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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

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Technology Process of (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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 5 articles about (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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: 75.0%

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-fluorophenyl)-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 (1427296-93-2) + N,N-dimethylethylenediamine (108-00-9) → (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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 (1427297-08-2)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 2h;

DOI:10.1038/nchem.1596

Reference yield: 75.0%

→ (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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 (1427297-08-2)

Guidance literature:

In tetrahydrofuran; at 60 ℃; for 2h; Inert atmosphere;

Reference yield:

geldanmycin (30562-34-6) → (4E,6Z,8S,9S,10E,12S,13R,14S,16R)-19-(2-(dimethylamino)ethylam)-21-(4-fluorophenyl)-13-hydroxy-8,14-dimethoxy-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 (1427297-08-2)

Guidance literature:

Multi-step reaction with 3 steps

1: iodine; pyridine

2: tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; triphenyl-arsane; copper(l) iodide / N,N-dimethyl-formamide / 35 °C

3: tetrahydrofuran / 2 h / 60 °C

With pyridine; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; copper(l) iodide; triphenyl-arsane; iodine; In tetrahydrofuran; N,N-dimethyl-formamide; 2: |Stille Cross Coupling;

DOI:10.1038/nchem.1596

upstream raw materials:

geldanmycin

(4E,6Z,8S,9S,10E,12S,13R,14S,16R)-21-(4-fluorophenyl)-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

N,N-dimethylethylenediamine

(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

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