(2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide

Base Information

• Chemical Name: (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide
• CAS No.: 191408-45-4
• Molecular Formula: C₃₂H₄₄N₄O₆
• Molecular Weight: 580.725

Synonyms:(2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide

Chemical Property of (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide

There total 10 articles about (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide 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:

trans-cinnamyl iodide (82859-39-0) → (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide (191408-45-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LDA, 2.) TMEDA / 1.) THF, from -45 to -20 deg C, 1.5 h, 2.) THF, from -45 to -20 deg C, 3 h

2: aq. NaOH / methanol

3: BOP, i-Pr₂NEt / dimethylformamide

4: 67 percent / NaH / dimethylformamide / 0 °C

5: 100 percent / HCl / dioxane

6: 1.) DBU / 1.) DMF, 2.) DMF

7: 85 percent / H₂ / Pd(OH)2/C / methanol

8: 78 percent / H₅IO₆, aq. RuCl₃ / acetonitrile; CCl₄

9: 26 percent / BOP, i-Pr₂NEt / dimethylformamide

With hydrogenchloride; ruthenium trichloride; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide (178932-85-9) → (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide (191408-45-4)

Guidance literature:

Multi-step reaction with 7 steps

1: BOP, i-Pr₂NEt / dimethylformamide

2: 67 percent / NaH / dimethylformamide / 0 °C

3: 100 percent / HCl / dioxane

4: 1.) DBU / 1.) DMF, 2.) DMF

5: 85 percent / H₂ / Pd(OH)2/C / methanol

6: 78 percent / H₅IO₆, aq. RuCl₃ / acetonitrile; CCl₄

7: 26 percent / BOP, i-Pr₂NEt / dimethylformamide

With hydrogenchloride; ruthenium trichloride; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

Cinnamyl bromide (4392-24-9) → (2S,3R,6S)-10-Acetyl-12-methyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2,6-dicarboxylic acid 2-(benzyloxy-amide) 6-methylamide (191408-45-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) LDA, 2.) TMEDA / 1.) THF, from -45 to -20 deg C, 1.5 h, 2.) THF, from -45 to -20 deg C, 3 h

2: aq. NaOH / methanol

3: BOP, i-Pr₂NEt / dimethylformamide

4: 67 percent / NaH / dimethylformamide / 0 °C

5: 100 percent / HCl / dioxane

6: 1.) DBU / 1.) DMF, 2.) DMF

7: 85 percent / H₂ / Pd(OH)2/C / methanol

8: 78 percent / H₅IO₆, aq. RuCl₃ / acetonitrile; CCl₄

9: 26 percent / BOP, i-Pr₂NEt / dimethylformamide

With hydrogenchloride; ruthenium trichloride; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; periodic acid; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1016/S0960-894X(99)00215-2

upstream raw materials:

trans-cinnamyl iodide

N-δ-tert-butoxycarbonyl-L-ornithine methyl amide

Cinnamyl bromide

2R,3S-4-Benzyloxy-3-hydroxy-2-(2E-3-phenyl-2-propen-1-yl)butyric acid

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