(2S)-N-[(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butyl]-3-(2H5)phenyl-2-(pyrazin-2-ylformamido)(2H3)propanamide

• ChemBase ID: 176736
• Molecular Formular: C29H39BN4O4
• Molecular Mass: 518.45536
• Monoisotopic Mass: 518.30643615
• SMILES: [C@H]12C([C@H]([C@]3([C@@H](C1)OB(O3)[C@@H](NC(=O)[C@@H](NC(=O)c1cnccn1)Cc1ccccc1)CC(C)C)C)C2)(C)C
• Canonical SMILES: CC(C[C@@H](B1O[C@H]2[C@](O1)(C)[C@@H]1C[C@H](C2)C1(C)C)NC(=O)[C@@H](NC(=O)c1cnccn1)Cc1ccccc1)C
• InChI: InChI=1S/C29H39BN4O4/c1-18(2)13-25(30-37-24-16-20-15-23(28(20,3)4)29(24,5)38-30)34-26(35)21(14-19-9-7-6-8-10-19)33-27(36)22-17-31-11-12-32-22/h6-12,17-18,20-21,23-25H,13-16H2,1-5H3,(H,33,36)(H,34,35)/t20-,21-,23-,24+,25-,29-/m0/s1
• InChIKey: HZCSTPSWJFWZHP-GQABWHEGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-N-[(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decan-4-yl]butyl]-3-(^2H₅)phenyl-2-(pyrazin-2-ylformamido)(^2H₃)propanamide
• IUPAC Traditional name: (2S)-N-[(1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.0^2,^6]decan-4-yl]butyl]-3-(^2H₅)phenyl-2-(pyrazin-2-ylformamido)(^2H₃)propanamide
• Synonyms: N-[(1S)-2-[[(1R)-1-[(3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]-2-oxo-1-(phenylmethyl)ethyl]-2-pyrazinecarboxamide; (1R)-(1S,2S,3R,5S)-Pinanediol-N-(N-pyrazinylphenylalaninoyl)-1-amino-3-methylbutane-1-boronate-d8

Database IDs

• PubChem SID: 164232646
• PubChem CID: 71751672

CALCULATED PROPERTIES

• Acid pKa: 13.192402
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 4.7426
• LogD (pH = 7.4): 4.7425995
• Log P: 4.7426
• Molar Refractivity: 138.7317 cm^3
• Polarizability: 56.537632 Å^3
• Polar Surface Area: 102.44 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dimethyl Sulfoxide; Ethanol; Ethyl Acetate
• Apperance: Yellow Solid

DETAILS

Toronto Research Chemicals - P458532

Intermediate in the preparation of Bortezomib (B675700), a dipeptidyl boronate proteasome inhibitor.

REFERENCES

• Zhu, Y., et al.: Bioorg. Med. Chem., 14, 1483 (2006)
• Dorsey, B., et al.: J. Med. Chem., 51, 1068 (2006)
• Zhu, Y., et al.: Eur. J .Med. Chem., 44, 1486 (2006)