(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

Base Information

Chemical Name:(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester
CAS No.:191408-30-7
Molecular Formula:C₂₈H₄₃N₃O₇
Molecular Weight:533.665
Hs Code.:

(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

Synonyms:

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Chemical Property of (2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

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Technology Process of (2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

There total 11 articles about (2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl 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:

: 82859-39-0
trans-cinnamyl iodide

: 191408-30-7
(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

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: 74 percent / NaH / dimethylformamide / 0 °C

5: 80 percent / HCl / dioxane

6: 1.) i-Pr₂NEt / 1.) acetonitrile, 2.) acetonitrile

7: H₂ / Pd/C / methanol

8: H₂ / Pd(OH)2/C

9: NaIO₄, aq. RuCl₃ / acetonitrile; CCl₄

With hydrogenchloride; ruthenium trichloride; sodium hydroxide; sodium periodate; N,N,N,N,-tetramethylethylenediamine; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

: 178932-85-9
N-δ-tert-butoxycarbonyl-L-ornithine methyl amide

: 191408-30-7
(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: BOP, i-Pr₂NEt / dimethylformamide

2: 74 percent / NaH / dimethylformamide / 0 °C

3: 80 percent / HCl / dioxane

4: 1.) i-Pr₂NEt / 1.) acetonitrile, 2.) acetonitrile

5: H₂ / Pd/C / methanol

6: H₂ / Pd(OH)2/C

7: NaIO₄, aq. RuCl₃ / acetonitrile; CCl₄

With hydrogenchloride; ruthenium trichloride; sodium periodate; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; palladium on activated charcoal; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(99)00215-2

Reference yield:

: 4392-24-9
Cinnamyl bromide

: 191408-30-7
(2S,3R,6S)-6-Methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotetradecane-2,10-dicarboxylic acid 10-tert-butyl ester

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: 74 percent / NaH / dimethylformamide / 0 °C

5: 80 percent / HCl / dioxane

6: 1.) i-Pr₂NEt / 1.) acetonitrile, 2.) acetonitrile

7: H₂ / Pd/C / methanol

8: H₂ / Pd(OH)2/C

9: NaIO₄, aq. RuCl₃ / acetonitrile; CCl₄

With hydrogenchloride; ruthenium trichloride; sodium hydroxide; sodium periodate; N,N,N,N,-tetramethylethylenediamine; hydrogen; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; palladium dihydroxide; palladium on activated charcoal; In 1,4-dioxane; methanol; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0960-894X(99)00215-2