(6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid

Base Information

• Chemical Name: (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid
• CAS No.: 191407-31-5
• Molecular Formula: C₂₉H₃₈N₂O₆
• Molecular Weight: 510.631

Synonyms:(6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid

Chemical Property of (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid

There total 12 articles about (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid 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:

(6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-10-carboxylic acid methyl ester (191408-61-4) → (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-10-carboxylic acid (191407-31-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jm010127e

Reference yield:

(R)-2-hexyl-3-(tert-butoxycarbonyl)propionic acid (200866-62-2) → (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-10-carboxylic acid (191407-31-5)

Guidance literature:

Multi-step reaction with 10 steps

1.1: LDA / tetrahydrofuran / 1 h / -78 °C

1.2: tetrahydrofuran / -78 - 20 °C

2.1: DBU / benzene / 4 h / Heating

3.1: 9-BBN / tetrahydrofuran / 12 h / 0 - 20 °C

3.2: aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

4.1: CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

5.1: H₂ / Pd/C / methanol / 3 h

6.1: NMM; TBTU / dimethylformamide / 2 h / 20 °C

7.1: Cs₂CO₃ / dimethylformamide; dimethylsulfoxide / 0.5 h / 80 °C

8.1: TFA / 1 h / 20 °C

9.1: NMM; HATU / dimethylformamide / 20 - 60 °C

10.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium diisopropyl amide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm010127e

Reference yield:

2-allyl-3-hexyl-succinic acid 1-tert-butyl ester → (6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1(15),12(16),13-triene-10-carboxylic acid (191407-31-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: DBU / benzene / 4 h / Heating

2.1: 9-BBN / tetrahydrofuran / 12 h / 0 - 20 °C

2.2: aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

3.1: CBr₄; PPh₃; imidazole / CH₂Cl₂ / 3.33 h / 0 - 20 °C

4.1: H₂ / Pd/C / methanol / 3 h

5.1: NMM; TBTU / dimethylformamide / 2 h / 20 °C

6.1: Cs₂CO₃ / dimethylformamide; dimethylsulfoxide / 0.5 h / 80 °C

7.1: TFA / 1 h / 20 °C

8.1: NMM; HATU / dimethylformamide / 20 - 60 °C

9.1: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

With 4-methyl-morpholine; 1H-imidazole; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; carbon tetrabromide; hydrogen; caesium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm010127e

upstream raw materials:

(6S,7R,10S)-6-Benzyloxycarbamoyl-7-hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-10-carboxylic acid methyl ester

O-benzylhydoxylamine hydrochloride

L-tyrosine methyl ester HCl

(R)-2-hexyl-3-(tert-butoxycarbonyl)propionic acid

Downstream raw materials:

(6S,7R,10S)-7-Hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-methylcarbamoylmethyl-amide

(6S,7R,10S)-7-Hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-{[2-(4-sulfamoyl-phenyl)-ethyl]-amide}

(6S,7R,10S)-7-Hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-[(3-imidazol-1-yl-propyl)-amide]

(6S,7R,10S)-7-Hexyl-8-oxo-2-oxa-9-aza-bicyclo[10.2.2]hexadeca-1⁽¹⁵⁾,12⁽¹⁶⁾,13-triene-6,10-dicarboxylic acid 6-(benzyloxy-amide) 10-[((S)-2-tert-butoxy-1-methylcarbamoyl-ethyl)-amide]

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