(9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester

Base Information

• Chemical Name: (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester
• CAS No.: 188446-17-5
• Molecular Formula: C₃₁H₃₃N₃O₈
• Molecular Weight: 575.618

Synonyms:(9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester

Chemical Property of (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester

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Technology Process of (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-hexaene-9-carboxylic acid methyl ester

There total 10 articles about (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3,5,7⁽¹⁹⁾,14⁽¹⁸⁾,15-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: 63.0%

(S)-2-[(S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(4-hydroxy-phenyl)-propionylamino]-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester (188446-15-3) → (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3,5,7(19),14(18),15-hexaene-9-carboxylic acid methyl ester (188446-17-5)

Guidance literature:

With sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; at 0 - 25 ℃; for 4.5h;

DOI:10.1021/jo961346o

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3,5,7(19),14(18),15-hexaene-9-carboxylic acid methyl ester (188446-17-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent

2: 76 percent / LiOH

3: 78 percent / EDCI, HOBt

4: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 4.5 h / 0 - 25 °C

With lithium hydroxide; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo961346o

Reference yield:

L-Tyr-OMe (1080-06-4) → (9S,12S)-12-(Benzyl-tert-butoxycarbonyl-amino)-4-nitro-11-oxo-2-oxa-10-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3,5,7(19),14(18),15-hexaene-9-carboxylic acid methyl ester (188446-17-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 99 percent / NaBH(OAc)3

2: 66 percent

3: 76 percent / LiOH

4: 78 percent / EDCI, HOBt

5: 63 percent / NaH / tetrahydrofuran; dimethylformamide / 4.5 h / 0 - 25 °C

With lithium hydroxide; sodium tris(acetoxy)borohydride; sodium hydride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/jo961346o

upstream raw materials:

(S)-2-[(S)-2-(Benzyl-tert-butoxycarbonyl-amino)-3-(4-hydroxy-phenyl)-propionylamino]-3-(3-fluoro-4-nitro-phenyl)-propionic acid methyl ester

di-tert-butyl dicarbonate

L-Tyr-OMe

benzaldehyde

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