(2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide

Base Information

• Chemical Name: (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide
• CAS No.: 191408-42-1
• Molecular Formula: C₃₂H₄₁N₃O₅
• Molecular Weight: 547.695

Synonyms:(2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide

Chemical Property of (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide

There total 10 articles about (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid 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:

(R)-benzyl glycidol (14618-80-5) → (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide (191408-42-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) n-BuLi, HMPA, 2.) NBS, aq. NaHCO₃ / 1.) THF

2: 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

3: aq. NaOH / methanol

4: BOP, i-Pr₂NEt / dimethylformamide

5: 67 percent / NaH / dimethylformamide / 0 °C

6: 100 percent / HCl / dioxane

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

With hydrogenchloride; N,N,N,N,N,N-hexamethylphosphoric triamide; sodium hydroxide; N-Bromosuccinimide; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; In 1,4-dioxane; methanol; N,N-dimethyl-formamide;

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

Reference yield:

Methyl (S)-4-(benzyloxy)-3-hydroxybutanoate (147849-60-3) → (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide (191408-42-1)

Guidance literature:

Multi-step reaction with 6 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

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

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

Reference yield:

trans-cinnamyl iodide (82859-39-0) → (2S,3R,6S)-10-Acetyl-2-benzyloxymethyl-12-methylene-4-oxo-3-((E)-3-phenyl-allyl)-1-oxa-5,10-diaza-cyclotridecane-6-carboxylic acid methylamide (191408-42-1)

Guidance literature:

Multi-step reaction with 6 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

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

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

upstream raw materials:

acetic anhydride

trans-cinnamyl iodide

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

(R)-benzyl glycidol

Downstream raw materials:

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

(2S,3R,6S)-10-Acetyl-12-methyl-6-methylcarbamoyl-4-oxo-3-(3-phenyl-propyl)-1-oxa-5,10-diaza-cyclotridecane-2-carboxylic acid

(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

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