(S)-N⁴-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide

Base Information

• Chemical Name: (S)-N⁴-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide
• CAS No.: 1564251-56-4
• Molecular Formula: C₅₀H₆₃BN₄O₇
• Molecular Weight: 842.884

Synonyms:

Chemical Property of (S)-N⁴-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide

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Technology Process of (S)-N⁴-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide

There total 4 articles about (S)-N⁴-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N¹-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide 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:

6-phenyl-pyridine-2-carboxylic acid (39774-28-2) + C38H56BN3O6 → (S)-N4-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide (1564251-56-4)

Guidance literature:

With pivaloyl chloride; triethylamine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/jm500045x

Reference yield:

C31H47BN2O7 (1564251-59-7) → (S)-N4-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide (1564251-56-4)

Guidance literature:

Multi-step reaction with 4 steps

1: hydrogen; palladium on activated charcoal / tetrahydrofuran / 1.5 h

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / -18 - 20 °C

3: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

4: triethylamine; pivaloyl chloride / dichloromethane / 3 h / 0 °C

With 1-hydroxy-7-aza-benzotriazole; palladium on activated charcoal; hydrogen; pivaloyl chloride; 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:

C43H64BN3O8 (1564251-65-5) → (S)-N4-(4-(benzyloxy)-3-((benzyloxy)methyl)butyl)-N1-((R)-3-methyl-1-((3aS,4S,6S,7aR)-3a,5,5-trimethylhexahydro-4,6-methanobenzo[d][1,3,2]dioxaborol-2-yl)butyl)-2-(6-phenylpicolinamido)succinamide (1564251-56-4)

Guidance literature:

Multi-step reaction with 2 steps

1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

2: triethylamine; pivaloyl chloride / dichloromethane / 3 h / 0 °C

With pivaloyl chloride; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jm500045x

upstream raw materials:

C₃₁H₄₇BN₂O₇

C₄₃H₆₄BN₃O₈

6-phenyl-pyridine-2-carboxylic acid

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