(9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-12-carboxylic acid methyl ester

Base Information

• Chemical Name: (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-12-carboxylic acid methyl ester
• CAS No.: 108969-85-3
• Molecular Formula: C₃₁H₃₂Br₂N₂O₉
• Molecular Weight: 736.411

Synonyms:

Chemical Property of (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-12-carboxylic acid methyl ester

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Technology Process of (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-12-carboxylic acid methyl ester

There total 7 articles about (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.1^3,7]nonadeca-1⁽¹⁷⁾,3⁽¹⁹⁾,5,14⁽¹⁸⁾,15-pentaene-12-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: 50.5%

methanol (67-56-1) + methyl N-Cbz-3,5-dibromo-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate (108969-77-3) → (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-5,16,17-tribromo-7-methoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),5,14(18),15-pentaene-12-carboxylic acid methyl ester (108969-84-2) + (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),5,14(18),15-pentaene-12-carboxylic acid methyl ester (108969-85-3)

Guidance literature:

With thallium(III) nitrate; at 4 ℃; for 18h;

DOI:10.1248/cpb.43.1325

Reference yield:

2,6-dibromo-N-methyltyrosine methyl ester (108969-87-5) → (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),5,14(18),15-pentaene-12-carboxylic acid methyl ester (108969-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 57.5 percent / N,N-dicyclohexylcarbodiimide / dioxane / 1 h / Ambient temperature

2: 50.5 percent / thallium(III) trinitrate / 18 h / 4 °C

With dicyclohexyl-carbodiimide; thallium(III) nitrate; In 1,4-dioxane;

DOI:10.1248/cpb.43.1325

Reference yield:

N-benzyloxycarbonyl-2,6-dibromo-N-methyltyrosine (108969-86-4) → (9S,12S)-9-(Benzyloxycarbonyl-methyl-amino)-16,17-dibromo-5,7-dimethoxy-11-methyl-4,10-dioxo-2-oxa-11-aza-tricyclo[12.2.2.13,7]nonadeca-1(17),3(19),5,14(18),15-pentaene-12-carboxylic acid methyl ester (108969-85-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 57.5 percent / N,N-dicyclohexylcarbodiimide / dioxane / 1 h / Ambient temperature

2: 50.5 percent / thallium(III) trinitrate / 18 h / 4 °C

With dicyclohexyl-carbodiimide; thallium(III) nitrate; In 1,4-dioxane;

DOI:10.1248/cpb.43.1325

upstream raw materials:

methanol

methyl N-Cbz-3,5-dibromo-N-methyl-L-tyrosyl-3,5-dibromo-N-methyl-L-tyrosinate

N-methyl-L-tyrosine

2,6-dibromo-N-methyltyrosine methyl ester

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