(8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester

Base Information

• Chemical Name: (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester
• CAS No.: 132149-69-0
• Molecular Formula: C₃₀H₃₁N₃O₈
• Molecular Weight: 561.591

Synonyms:(8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester

Chemical Property of (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester

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Technology Process of (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl ester

There total 4 articles about (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]henicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carboxylic acid methyl 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: 49.0%

(S)-3-{5'-[(S)-2-((S)-2-Amino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-2-benzyloxycarbonylamino-propionic acid 4-nitro-phenyl ester → (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(20),2,4,6(21),16,18-hexaene-8-carboxylic acid methyl ester (132149-69-0)

Guidance literature:

With pyridine; benzotriazol-1-ol; In N,N-dimethyl-formamide; at 100 ℃;

DOI:10.1016/S0040-4039(00)97122-3

Reference yield:

L-Tyr-OMe (1080-06-4) → (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(20),2,4,6(21),16,18-hexaene-8-carboxylic acid methyl ester (132149-69-0)

Guidance literature:

Multi-step reaction with 4 steps

1: DCC, HOBT / tetrahydrofuran; dimethylformamide

2: 7 percent / VOCl₃ / tetrahydrofuran / 2 h / -60 deg C -> 0 deg C

3: 100 percent / TFA / CH₂Cl₂ / Ambient temperature

4: 49 percent / pyridine, HOBT / dimethylformamide / 100 °C

With pyridine; vanadium(V) oxychloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97122-3

Reference yield:

L-N-Boc-Ala-L-Tyr methyl ester (84794-40-1) → (8S,11S,14S)-14-Benzyloxycarbonylamino-3,19-dihydroxy-11-methyl-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]henicosa-1(20),2,4,6(21),16,18-hexaene-8-carboxylic acid methyl ester (132149-69-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 7 percent / VOCl₃ / tetrahydrofuran / 2 h / -60 deg C -> 0 deg C

2: 100 percent / TFA / CH₂Cl₂ / Ambient temperature

3: 49 percent / pyridine, HOBT / dimethylformamide / 100 °C

With pyridine; vanadium(V) oxychloride; benzotriazol-1-ol; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)97122-3

upstream raw materials:

L-Tyr-OMe

L-N-Boc-Ala-L-Tyr methyl ester

(S)-2-Benzyloxycarbonylamino-3-{5'-[(S)-2-((S)-2-tert-butoxycarbonylamino-propionylamino)-2-methoxycarbonyl-ethyl]-6,2'-dihydroxy-biphenyl-3-yl}-propionic acid 4-nitro-phenyl ester

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