tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

Base Information

Chemical Name:tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate
CAS No.:191408-12-5
Molecular Formula:C₃₁H₅₁N₃O₆S
Molecular Weight:593.828
Hs Code.:

Synonyms:tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

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Chemical Property of tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

Chemical Property:

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Technology Process of tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

There total 5 articles about tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate 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:

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

: 191408-12-5
tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: H₂ / Pd/C / methanol / 3 h

2: BOP; DIEA / dimethylformamide

3: DIAD; PPh₃ / tetrahydrofuran

With di-isopropyl azodicarboxylate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 3: Mitsunobu reaction;
DOI:10.1021/jm010127e

Reference yield:

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

: 191408-12-5
tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

Guidance literature:: Multi-step reaction with 4 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: H₂ / Pd/C / methanol / 3 h

3.1: BOP; DIEA / dimethylformamide

4.1: DIAD; PPh₃ / tetrahydrofuran

With 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 4.1: Mitsunobu reaction;
DOI:10.1021/jm010127e

Reference yield:

: 184489-29-0
(2R)-3-(tert-butoxycarbonyl)-2-isobutyl-5-hexenoic acid

: 191408-12-5
tert-butyl (6S,9R,10S)-9-isobutyl-6-[(methylamino)carbonyl]-8-oxo-1-(mesitylsulfonyl)-1,7-diazacyclotridecane-10-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: 62 percent / DBU / benzene / 4 h / Heating

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

2.2: 64 percent / aq. H₂O₂; AcONa / tetrahydrofuran / 0.33 h / 0 °C

3.1: H₂ / Pd/C / methanol / 3 h

4.1: BOP; DIEA / dimethylformamide

5.1: DIAD; PPh₃ / tetrahydrofuran

With 9-borabicyclo[3.3.1]nonane dimer; di-isopropyl azodicarboxylate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; benzene; 5.1: Mitsunobu reaction;
DOI:10.1021/jm010127e