(S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide

Base Information

• Chemical Name: (S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide
• CAS No.: 188633-86-5
• Molecular Formula: C₂₈H₄₃N₃O₇S
• Molecular Weight: 565.731

Synonyms:(S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide

Chemical Property of (S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide

Chemical Property:

Purity/Quality:

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Technology Process of (S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide

There total 3 articles about (S_S)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide 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: 68.0%

L-isoleucine-allyl ester tosylate + cyclohexyl(isopropyl)ammonium (SS)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl)-S-methyl S-phenyl sulfonimidoyl acetate → (SS)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide (188633-86-5)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide;

DOI:10.1016/S0040-4039(97)00001-4

Reference yield:

(SS)-N-(N-tert-Butyloxycarbonyl-L-isoleucinyl)-S-methyl S-phenyl sulfoximine (188633-72-9) → (SS)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide (188633-86-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: nBuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

1.3: 82 percent / tetrahydrofuran; hexane / -78 - 20 °C

2.1: 68 percent / DMAP; DCC / CH₂Cl₂ / 13 h / 0 - 20 °C

With dmap; n-butyllithium; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/1521-3765(20010302)7:5<1118::AID-CHEM1118>3.0.CO;2-3

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → (SS)-N-(N-tert-butyloxycarbonyl-L-isoleucinyl S-phenyl sulfonimidoyl methyl)-N-(O-allyl-L-isoleucinyl)carboxyamide (188633-86-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 93 percent / HOBt; DCC / CH₂Cl₂ / 13 h / 0 - 20 °C

2.1: nBuLi / tetrahydrofuran; hexane / 0.5 h / 0 °C

2.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.3: 82 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 68 percent / DMAP; DCC / CH₂Cl₂ / 13 h / 0 - 20 °C

With dmap; n-butyllithium; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1002/1521-3765(20010302)7:5<1118::AID-CHEM1118>3.0.CO;2-3

upstream raw materials:

N-(tert-butyloxycarbonyl)-L-isoleucine

(S_S)-N-(N-tert-Butyloxycarbonyl-L-isoleucinyl)-S-methyl S-phenyl sulfoximine

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