Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl ester

Base Information

• Chemical Name: Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl ester
• CAS No.: 448235-62-9
• Molecular Formula: C₄₀H₅₅N₅O₁₁
• Molecular Weight: 781.904

Synonyms:

Chemical Property of Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl ester

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Technology Process of Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl ester

There total 2 articles about Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1⁽²¹⁾,4,6,10,18-pentaen-9-yl ester 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: 73.0%

4-maleimidobutyric acid N-hydroxysuccinimide ester (80307-12-6) + 17-(4-aminobutyloamino)-17-demethoxy geldanamycin → Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl ester (448235-62-9)

Guidance literature:

In ethyl acetate;

DOI:10.1016/S0960-894X(00)00155-4

Reference yield:

geldanmycin (30562-34-6) → Carbamic acid (4E,6Z,10E)-(8S,9S,12S,13R,14S,16R)-19-{4-[4-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-butyrylamino]-butylamino}-13-hydroxy-8,14-dimethoxy-4,10,12,16-tetramethyl-3,20,22-trioxo-2-aza-bicyclo[16.3.1]docosa-1(21),4,6,10,18-pentaen-9-yl ester (448235-62-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / CHCl₃

2: 73 percent / ethyl acetate

In chloroform; ethyl acetate; 1: Substitution / 2: Acylation;

DOI:10.1016/S0960-894X(00)00155-4

upstream raw materials:

4-maleimidobutyric acid N-hydroxysuccinimide ester

geldanmycin

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