tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-(2H5)phenylethyl]carbamate

• ChemBase ID: 162501
• Molecular Formular: C15H21NO3
• Molecular Mass: 263.33214
• Monoisotopic Mass: 263.15214354
• SMILES: C1[C@H]([C@H](Cc2ccccc2)NC(=O)OC(C)(C)C)O1
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H]([C@@H]1OC1)Cc1ccccc1
• InChI: InChI=1S/C15H21NO3/c1-15(2,3)19-14(17)16-12(13-10-18-13)9-11-7-5-4-6-8-11/h4-8,12-13H,9-10H2,1-3H3,(H,16,17)/t12-,13+/m0/s1
• InChIKey: NVPOUMXZERMIJK-QWHCGFSZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-(^2H₅)phenylethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-(^2H₅)phenylethyl]carbamate
• Synonyms: N-[(1S)-1-[(2R)-2-Oxiranyl]-2-(phenyl-d5)-ethyl]-carbamic Acid 1,1-Dimethylethyl Ester; (2S,3R)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenyl-d5-butane; [(1S)-1-(2R)-Oxiranyl-2-(phenyl-d5)-ethyl]carbamic Acid tert-Butyl Ester; (2R,3S)-3-Boc-amino-1,2-epoxy-4-phenyl-d5-butane

Database IDs

• CAS Number: 856765-76-9
• PubChem SID: 162256636
• PubChem CID: 11196449

CALCULATED PROPERTIES

• Acid pKa: 14.284454
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 2.7808065
• LogD (pH = 7.4): 2.7808065
• Log P: 2.7808065
• Molar Refractivity: 72.5743 cm^3
• Polarizability: 28.788164 Å^3
• Polar Surface Area: 47.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Diethyl Ether
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - B618532

Atazanavir intermediate. Enantiomer R.

REFERENCES

• Vassar, R., et al.: Science, 286, 735 (1999)
• Maillard, M., et al.: J. Med. Chem., 50, 776 (1999)
• Stauffer, S., et al.: Bioorg. Med. Chem. Lett., 17, 1788 (2007)