Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-

Base Information

• Chemical Name: Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-
• CAS No.: 1132709-16-0
• Molecular Formula: C₁₉H₂₅BN₄O₄
• Molecular Weight: 384.243
• Mol file: 1132709-16-0.mol

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

Chemical Property of Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-

Chemical Property:

• PKA: 9.66±0.43(Predicted)
• PSA: 124.44000
• Density: 1.214±0.06 g/cm3(Predicted)
• LogP: 1.56230

Purity/Quality:

99%min. ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1S,3R)-Bortezomib is an 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 Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]-

There total 89 articles about Boronic acid, B-[(1S)-3-Methyl-1-[[(2R)-1-oxo-3-phenyl-2-[(2-pyrazinylcarbonyl)aMino]propyl]aMino]butyl]- 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: 77.0%

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide (205393-22-2) → velcade (179324-69-7,1132709-16-0)

Guidance literature:

With hydrogenchloride; Dihydroxy-isobutyl-boran; In water; at 20 ℃; Solvent; Temperature;

Reference yield: 52.0%

bortezomib pinacol ester (1029701-48-1) → velcade (179324-69-7,1132709-16-0)

Guidance literature:

With hydrogenchloride; 2-methyl-propan-1-ol; In methanol; pentane; at 0 - 20 ℃; for 12h;

Reference yield:

2-pyrazylcarboxylic acid (98-97-5) + (CH3)2CHCH2CH(BO2C2(CH3)4)NHCOCH(CH2C6H5)NH3(1+)*Cl(1-)=(CH3)2CHCH2CH(BO2C2(CH3)4)NHCOCH(CH2C6H5)NH3Cl (1029701-41-4) → velcade (179324-69-7,1132709-16-0)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine; In not given; 1. (2-pyrazine)CO2H, TBTU, i-Pr2EtN, 0°C - room temp.; 2. i-BuB(OH)2, pentane, MeOH, 1 N HCl;

DOI:10.1021/ja800829y

upstream raw materials:

bortezomib pinacol ester

2-pyrazylcarboxylic acid

(CH₃)2CHCH₂CH(BO₂C₂(CH₃)4)NHCOCH(CH₂C₆H₅)NH₃⁽¹⁺⁾*Cl^(1-)=(CH₃)2CHCH₂CH(BO₂C₂(CH₃)4)NHCOCH(CH₂C₆H₅)NH₃Cl

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

Downstream raw materials:

methyl (pyrazine-2-carbonyl)phenylalaninate

N-(1-(((R)-1-hydroxy-3-methylbutyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

N-(1-(((S)-1-hydroxy-3-methylbutyl)amino)-1-oxo-3-phenylpropan-2-yl)pyrazine-2-carboxamide

Phenylalanine

Refernces

• 1、 Kingsley, Laura J.,He, Xiaohui,McNeill, Matthew,Nelson, John,Nikulin, Victor,Ma, Zhiwei,Lu, Wenshuo,Zhou, Vicki W.,Manuia, Mari,Kreusch, Andreas,Gao, Mu-Yun,Witmer, Darbi,Vaillancourt, Mei-Ting,Lu, Min,Greenblatt, Sarah,Lee, Christian,Vashisht, Ajay,Bender, Steven,Spraggon, Glen,Michellys, Pierre-Yves,Jia, Yong,Haling, Jacob R.,Lelais, Gérald. "Structure-Based Design of Selective LONP1 Inhibitors for Probing in Vitro Biology". . p. 4857 - 4869. Retrieved 2021/05/07.
• 2、 Reyes, Ronald L.,Sato, Miyu,Iwai, Tomohiro,Sawamura, Masaya. "Asymmetric Synthesis of α-Aminoboronates via Rhodium-Catalyzed Enantioselective C(sp3)-H Borylation". . p. 589 - 597. Retrieved 2020/01/22.