(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

Base Information

Chemical Name:(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid
CAS No.:191407-57-5
Molecular Formula:C₂₆H₃₉N₃O₇
Molecular Weight:505.612
Hs Code.:

Synonyms:(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

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Chemical Property of (8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

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Technology Process of (8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

There total 12 articles about (8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-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:

: 191407-56-4
(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid methyl ester

: 191407-57-5
(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

Guidance literature:: With lithium hydroxide; In tetrahydrofuran; at 20 ℃; for 1h;
DOI:10.1021/jm010127e

Reference yield:

: 191406-75-4
4-benzyl 1-tert-butyl (2S,3R)-2-(3-hydroxypropyl)-3-isobutylbutanedioate

: 191407-57-5
(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 91 percent / NMM / CH₂Cl₂ / 20 °C

2: K₂CO₃ / dimethylformamide / 2 h / 50 °C

3: H₂ / Pd/C / methanol / 1 h

4: BOP; DIEA / dimethylformamide; CHCl₃ / 20 °C

5: TFA / CH₂Cl₂ / 1 h

6: DIEA; BOP / dimethylformamide / 20 °C

7: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm010127e

Reference yield:

: 191406-74-3
(2R,3S)-3-(tert-butoxycarbonyl)-2-isobutylhex-5-enoic acid benzyl ester

: 191407-57-5
(8S,11R,12S)-12-Benzyloxycarbamoyl-11-isobutyl-3-methyl-2,10-dioxo-1-oxa-3,9-diaza-cyclopentadecane-8-carboxylic acid

Guidance literature:: Multi-step reaction with 8 steps

1.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C

1.2: 64 percent / aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

2.1: 91 percent / NMM / CH₂Cl₂ / 20 °C

3.1: K₂CO₃ / dimethylformamide / 2 h / 50 °C

4.1: H₂ / Pd/C / methanol / 1 h

5.1: BOP; DIEA / dimethylformamide; CHCl₃ / 20 °C

6.1: TFA / CH₂Cl₂ / 1 h

7.1: DIEA; BOP / dimethylformamide / 20 °C

8.1: aq. LiOH / tetrahydrofuran / 1 h / 20 °C

With 4-methyl-morpholine; lithium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; hydrogen; potassium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; chloroform; N,N-dimethyl-formamide;
DOI:10.1021/jm010127e