benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate

Base Information

• Chemical Name: benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate
• CAS No.: 1264223-88-2
• Molecular Formula: C₃₃H₄₂N₄O₇S
• Molecular Weight: 638.785

Synonyms:benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate

Chemical Property of benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate

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Technology Process of benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate

There total 17 articles about benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1⁽²²⁾,18,20-triene-15-carboxylate 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: 57.0%

C33H44N4O8S (1264243-25-5) → benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.04,8]docosa-1(22),18,20-triene-15-carboxylate (1264223-88-2)

Guidance literature:

With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine; In dichloromethane; ethyl acetate; at 20 ℃; for 3h;

Reference yield: 57.0%

→ benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.04,8]docosa-1(22),18,20-triene-15-carboxylate (1264223-88-2)

Guidance literature:

Reference yield:

C21H22N2O8S (1264239-47-5) → benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-9,12,17-trioxo-2-thia-8,11,16-triazatricyclo[16.3.1.04,8]docosa-1(22),18,20-triene-15-carboxylate (1264223-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / N,N-dimethyl-formamide / 4 h / 0 - 20 °C

2.1: thiophenol; caesium carbonate / acetonitrile / 16 h / 20 °C

2.2: 0.08 h

3.1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 16 h / 0 - 20 °C

4.1: 1-amino-3-(dimethylamino)propane / tetrahydrofuran / 1 h / 20 °C

5.1: cyanomethylenetributyl-phosphorane / toluene / 0.5 h / 100 °C

5.2: 1 h / 100 °C

6.1: 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / dichloromethane; ethyl acetate / 0.5 h / 20 °C

7.1: 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; N-ethyl-N,N-diisopropylamine / dichloromethane; ethyl acetate / 3 h / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; 1,3-dimethylbarbituric acid; caesium carbonate; thiophenol; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-amino-3-(dimethylamino)propane; N-ethyl-N,N-diisopropylamine; cyanomethylenetributyl-phosphorane; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; acetonitrile;

upstream raw materials:

N-α-(t-butoxycarbonyl)-L-glutamic γ-allyl ester

C₁₅H₁₉NO₄*ClH

C₂₁H₂₂N₂O₈S

C₂₂H₂₄N₂O₈S

Downstream raw materials:

benzyl (4S,6R,15S)-6-[(tert-butoxycarbonyl)amino]-11,16-dimethyl-2,2,9,12,17-pentaoxo-2λ⁶-thia-8,11,16-triazatricyclo[16.3.1.0^4,8]docosa-1(22),18,20-triene-15-carboxylate

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