(R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate

Base Information

• Chemical Name: (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate
• CAS No.: 1427297-14-0
• Molecular Formula: C₃₈H₅₇N₅O₁₁S
• Molecular Weight: 791.963

Synonyms:(R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate

Chemical Property of (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate

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Technology Process of (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate

There total 2 articles about (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate 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: 21.0%

17-(2-(dimethylamino)ethylamino)(demethoxy)geldanamycin hydrochloride + Ac-Cys-OMe (7652-46-2) → (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate (1427297-14-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 48h;

Reference yield: 21.0%

Ac-Cys-OMe (7652-46-2) + alvespimycin (467214-20-6) → (R)-methyl-2-acetamido-3-((4E,6Z,8S,9S,10E,12S,13R,14S,16R)-9-(carbamoyloxy)-19-(2-(dimethylamino)ethylamino)-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-21-ylthio)propanoate (1427297-14-0)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃;

DOI:10.1038/nchem.1596

upstream raw materials:

Ac-Cys-OMe

alvespimycin

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