(S)-2-acetamido-N⁵-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide

Base Information

• Chemical Name: (S)-2-acetamido-N⁵-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide
• CAS No.: 1564251-51-9
• Molecular Formula: C₄₂H₆₂BN₃O₇
• Molecular Weight: 731.781

Synonyms:

Chemical Property of (S)-2-acetamido-N⁵-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide

Chemical Property:

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Technology Process of (S)-2-acetamido-N⁵-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide

There total 6 articles about (S)-2-acetamido-N⁵-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide 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: 75.0%

C20H27NO2 (1564251-64-4) + C22H37BN2O6 → (S)-2-acetamido-N5-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide (1564251-51-9)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h; Cooling;

DOI:10.1021/jm500045x

Reference yield:

C32H49BN2O7 (1564251-60-0) → (S)-2-acetamido-N5-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide (1564251-51-9)

Guidance literature:

Multi-step reaction with 4 steps

1: trifluoroacetic acid / dichloromethane / 15 h / 0 - 20 °C

2: triethylamine / dichloromethane / 0.42 h / 0 - 20 °C

3: hydrogen; palladium on activated charcoal / tetrahydrofuran / 3 h

4: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling

With 1-hydroxy-7-aza-benzotriazole; palladium on activated charcoal; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm500045x

Reference yield:

(S)-benzyl 4-acetamido-5-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-5-oxopentanoate (1564251-62-2) → (S)-2-acetamido-N5-(5-(benzyloxy)-4-((benzyloxy)methyl)pentyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)pentanediamide (1564251-51-9)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 3 h

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / Cooling

With 1-hydroxy-7-aza-benzotriazole; palladium on activated charcoal; hydrogen; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm500045x

upstream raw materials:

C₃₂H₄₉BN₂O₇

(S)-benzyl 4-acetamido-5-(((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)amino)-5-oxopentanoate

C₂₀H₂₇NO₂

Boc-Glu(OBzl)-OH

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