(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]butan-1-amine; trifluoroacetic acid

• ChemBase ID: 176734
• Molecular Formular: C17H29BF3NO4
• Molecular Mass: 379.2226696
• Monoisotopic Mass: 379.21417347
• SMILES: [C@H]12C([C@H]([C@]3([C@@H](C1)OB(O3)[C@H](CC(C)C)N)C)C2)(C)C.C(F)(F)(F)C(=O)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC(C[C@@H](B1O[C@H]2[C@](O1)(C)[C@@H]1C[C@H](C2)C1(C)C)N)C
• InChI: InChI=1S/C15H28BNO2.C2HF3O2/c1-9(2)6-13(17)16-18-12-8-10-7-11(14(10,3)4)15(12,5)19-16;3-2(4,5)1(6)7/h9-13H,6-8,17H2,1-5H3;(H,6,7)/t10-,11-,12+,13-,15-;/m0./s1
• InChIKey: SRFQKJZNJYTMNI-CDVUYJLHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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]butan-1-amine; trifluoroacetic acid
• IUPAC Traditional name: (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]butan-1-amine; trifluoroacetic acid
• Synonyms: (αR,3aS,4S,6S,7aR)-Hexahydro-3a,5,5-trimethyl-α-(2-methylpropyl)-4,6-methano-1,3,2-benzodioxaborole-2-methanamine 2,2,2-Trifluoroacetate; (1R)-(S)-Pinanediol-1-ammoniumtrifluoroacetate-3-methylbutane-1-boronate; (αR)-(1S,2S,3R,5S)-Pinanediol-1-amino-3-methylbutane-1-boronate Trifluoroacetate; (R)-BoroLeu-(+)-Pinanediol trifluoroacetate

Database IDs

• CAS Number: 179324-87-9
• MDL Number: MFCD10566030
• PubChem SID: 164232644
• PubChem CID: 44244713

CALCULATED PROPERTIES

• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.97919554
• LogD (pH = 7.4): 2.3768718
• Log P: 4.2635
• Molar Refractivity: 71.3868 cm^3
• Polarizability: 31.071415 Å^3
• Polar Surface Area: 44.48 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethylformamide; Methanol
• Apperance: White Solid
• Melting Point: 159-161°C

Safety Information

• Storage Condition: -20°C Freezer

Product Information

• Purity: 95+%

DETAILS

Toronto Research Chemicals - P458505

Bortezomib (B675700) intermediate. A boronic acid dipeptide derivative as proteasome inhibitors.

REFERENCES

• Kisselev, A., et al.: Chem. Biol., 8, 739 (2001)
• Kisselev, A., et al.: J. Biol. Chem., 278, 35869 (2001)
• Verdoes, M., et al.: Chem. Biol., 13, 1217 (2001)