((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid

Base Information

• Chemical Name: ((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid
• CAS No.: 1132709-15-9
• Molecular Formula: C₁₉H₂₅BN₄O₄
• Molecular Weight: 384.243
• Hs Code.: 2934999090
• Mol file: 1132709-15-9.mol

Synonyms:((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid;(1R,2R)-BortezoMib;N-(2-Pyrazinecarbonyl)-D-phenylalanine-L-leucine boronic anhydride;[(1R)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)amino]propyl]amino]butyl]boronic acid

Chemical Property of ((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid

Chemical Property:

• PKA: 9.66±0.43(Predicted)
• PSA: 131.42000
• Density: 1.214±0.06 g/cm3(Predicted)
• LogP: 2.19560
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(1R,2R)-Bortezomib ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (1R,2R)-Bortezomib is a diastereomer of Bortezomib (B675700), the first proteasome inhibitor to be approved by the US FDA for multiple myeloma, a blood cancer. A reversible inhibitor of the 26S proteasome-a barrel-shaped multiprotein particle found in the nucleus and cytosol of all eukaryotic cells. Targets the ubiquitin-proteasome pathway

Technology Process of ((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic acid

There total 4 articles about ((R)-3-Methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxaMido)propanaMido)butyl)boronic 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:

Boc-D-Phe-OH (18942-49-9) → ((R)-3-methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid (1132709-15-9,1132709-16-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 0.08 h / -15 °C

1.2: -15 - 20 °C

2.1: hydrogenchloride / 1,4-dioxane / 16 h

3.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 0.08 h / -15 °C

3.2: -15 - 20 °C

4.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 16 h

With hydrogenchloride; Dihydroxy-isobutyl-boran; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; n-heptane;

DOI:10.1021/acs.jmedchem.0c02152

Reference yield:

C29H45BN2O5 → ((R)-3-methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid (1132709-15-9,1132709-16-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: hydrogenchloride / 1,4-dioxane / 16 h

2.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 0.08 h / -15 °C

2.2: -15 - 20 °C

3.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 16 h

With hydrogenchloride; Dihydroxy-isobutyl-boran; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In 1,4-dioxane; methanol; n-heptane;

DOI:10.1021/acs.jmedchem.0c02152

Reference yield:

C24H37BN2O3*ClH → ((R)-3-methyl-1-((R)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)butyl)boronic acid (1132709-15-9,1132709-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate / 0.08 h / -15 °C

1.2: -15 - 20 °C

2.1: hydrogenchloride; Dihydroxy-isobutyl-boran / methanol; n-heptane / 16 h

With hydrogenchloride; Dihydroxy-isobutyl-boran; N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In methanol; n-heptane;

DOI:10.1021/acs.jmedchem.0c02152

upstream raw materials:

Boc-D-Phe-OH

Refernces