(10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl ester

Base Information

• Chemical Name: (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl ester
• CAS No.: 890139-94-3
• Molecular Formula: C₃₅H₄₉N₅O₉Si
• Molecular Weight: 711.888

Synonyms:(10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl ester

Chemical Property of (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl ester

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Technology Process of (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl ester

There total 6 articles about (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.1^5,8]henicosa-1⁽¹⁹⁾,5⁽²¹⁾,6,17-tetraene-18,19-dicarboxylic acid dimethyl 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: 67.0%

3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate (890139-50-1) → (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.15,8]henicosa-1(19),5(21),6,17-tetraene-18,19-dicarboxylic acid dimethyl ester (890139-94-3)

Guidance literature:

With copper(l) iodide; N-ethyl-N,N-diisopropylamine; In toluene; at 20 ℃; for 12h;

DOI:10.1021/ol0604724

Reference yield:

3-Oxo-3-((S)-2-oxo-5-triisopropylsilanyloxymethyl-pyrrolidin-1-yl)-propionic acid → (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.15,8]henicosa-1(19),5(21),6,17-tetraene-18,19-dicarboxylic acid dimethyl ester (890139-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.06 g / DMAP; diisopropylcarbodiimide / CH₂Cl₂ / 12 h

2: 93 percent / MsN₃; Et₃N / acetonitrile

3: Rh₂Oct₄ / benzene / 1.5 h / 95 °C

4: 210 mg / benzene / 12 h / 20 °C

5: 67 percent / N,N-diisopropylethylamine; CuI / toluene / 12 h / 20 °C

With dmap; copper(l) iodide; triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonyl azide; diisopropyl-carbodiimide; rhodium (II) octanoate dimer; In dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1021/ol0604724

Reference yield:

(S)-prop-2-ynyl 3-oxo-3-(2-oxo-5-((triisopropylsilyloxy)methyl)pyrrolidin-1-yl)propanoate (890139-47-6) → (10S,14S)-10-Benzyl-2,12-dioxo-14-triisopropylsilanyloxymethyl-3,20-dioxa-6,7,8,11,13-pentaaza-tricyclo[15.2.1.15,8]henicosa-1(19),5(21),6,17-tetraene-18,19-dicarboxylic acid dimethyl ester (890139-94-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / MsN₃; Et₃N / acetonitrile

2: Rh₂Oct₄ / benzene / 1.5 h / 95 °C

3: 210 mg / benzene / 12 h / 20 °C

4: 67 percent / N,N-diisopropylethylamine; CuI / toluene / 12 h / 20 °C

With copper(l) iodide; triethylamine; N-ethyl-N,N-diisopropylamine; Methanesulfonyl azide; rhodium (II) octanoate dimer; In toluene; acetonitrile; benzene;

DOI:10.1021/ol0604724

upstream raw materials:

3,4-dimethyl 2-prop-2-ynyl 5-((S)-3-(3-((S)-1-azido-3-phenylpropan-2-yl)ureido)-4-(triisopropylsilyloxy)butyl)furan-2,3,4-tricarboxylate

(S)-prop-2-ynyl 3-oxo-3-(2-oxo-5-((triisopropylsilyloxy)methyl)pyrrolidin-1-yl)propanoate

2-Diazo-3-oxo-3-((S)-2-oxo-5-triisopropylsilanyloxymethyl-pyrrolidin-1-yl)-propionic acid prop-2-ynyl ester

(S)-(+)-5-(triisopropylsilyloxymethyl)-pyrrolidin-2-one

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