(9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

Base Information

• Chemical Name: (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester
• CAS No.: 291781-70-9
• Molecular Formula: C₃₂H₃₆N₄O₈
• Molecular Weight: 604.66

Synonyms:(9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

Chemical Property of (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

Chemical Property:

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Technology Process of (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

There total 10 articles about (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-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: 85.0%

(9S,12S,15S)-15-Acetylamino-4-methoxy-12-(4-methoxy-benzyl)-19-nitro-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carboxylic acid methyl ester (291781-69-6) → (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carboxylic acid methyl ester (291781-70-9)

Guidance literature:

With tetrafluoroboric acid; hydrogen; palladium on activated charcoal; In methanol;

DOI:10.1016/S0040-4039(00)00695-X

Reference yield:

methyl (S)-2-amino-3-(4-methoxyphenyl)propionate (17355-19-0) → (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carboxylic acid methyl ester (291781-70-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / EDC; HOBt

2: LiOH / tetrahydrofuran; H₂O

3: EDC; HOBt

4: BCl₃

6: 99 percent / K₂CO₃ / dimethylsulfoxide / 24 h / 20 °C

7: TFA

8: NaHCO₃ / tetrahydrofuran

9: 85 percent / H₂; HBF₄ / Pd/C / methanol

With lithium hydroxide; tetrafluoroboric acid; hydrogen; boron trichloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; 1: Dehydration / 2: Hydrolysis / 3: Condensation / 4: dealkyation / 5: Acylation / 6: Cyclization / 7: Hydrolysis / 8: Acetylation / 9: Reduction;

DOI:10.1016/S0040-4039(00)00695-X

Reference yield:

(S)-N-(tert-butyloxycarbonyl)-4-fluoro-3-nitrophenylalanine → (9S,12S,15S)-15-Acetylamino-19-amino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.13,7]docosa-1(20),3,5,7(22),17(21),18-hexaene-9-carboxylic acid methyl ester (291781-70-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 85 percent / EDC; HOBt

2: LiOH / tetrahydrofuran; H₂O

3: EDC; HOBt

4: BCl₃

6: 99 percent / K₂CO₃ / dimethylsulfoxide / 24 h / 20 °C

7: TFA

8: NaHCO₃ / tetrahydrofuran

9: 85 percent / H₂; HBF₄ / Pd/C / methanol

With lithium hydroxide; tetrafluoroboric acid; hydrogen; boron trichloride; sodium hydrogencarbonate; potassium carbonate; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; water; dimethyl sulfoxide; 1: Dehydration / 2: Hydrolysis / 3: Condensation / 4: dealkyation / 5: Acylation / 6: Cyclization / 7: Hydrolysis / 8: Acetylation / 9: Reduction;

DOI:10.1016/S0040-4039(00)00695-X

upstream raw materials:

(9S,12S,15S)-15-Acetylamino-4-methoxy-12-(4-methoxy-benzyl)-19-nitro-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

methyl (S)-2-amino-3-(4-methoxyphenyl)propionate

(S)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-3-nitro-phenyl)-propionylamino]-3-(4-methoxy-phenyl)-propionic acid methyl ester

(9S,12S,15S)-15-Amino-4-methoxy-12-(4-methoxy-benzyl)-19-nitro-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

Downstream raw materials:

(9S,12S,15S)-15-Acetylamino-4-methoxy-12-(4-methoxy-benzyl)-11,14-dioxo-2-oxa-10,13-diaza-tricyclo[15.2.2.1^3,7]docosa-1⁽²⁰⁾,3,5,7⁽²²⁾,17⁽²¹⁾,18-hexaene-9-carboxylic acid methyl ester

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