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

• ChemBase ID: 67544
• 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-phenylethyl]carbamate
• IUPAC Traditional name: tert-butyl N-[(1S)-1-[(2S)-oxiran-2-yl]-2-phenylethyl]carbamate
• Synonyms: (2S,3S)-N-t-Boc-3-amino-1,2-epoxy-4-phenylbutane; N-[(1S)-1-[(2S)-2-Oxiranyl]-2-phenylethyl]-carbamic Acid 1,1-Dimethylethyl Ester; (2S,3S)-(-)-3-tert-Butoxycarbonylamino-1,2-epoxy-4-phenylbutane; [(1S)-1-((2S)-Oxiranyl)-2-phenylethyl]carbamic Acid tert-Butyl Ester; (2S,3S)-3-Boc-amino-1,2-epoxy-4-phenylbutane; tert-Butyl [S-(R*,R*)]-(-)-(1-oxiranyl-2-phenylethyl)carbamate; (2S,3S)-1,2-Epoxy-3-(Boc-amino)-4-phenylbutane; [S-(R*,R*)]-(-)-(1-环氧乙基-2-苯乙基)氨基甲酸叔丁酯; (2S,3S)-1,2-环氧-3-(Boc-氨基)-4-苯基丁烷

Database IDs

• CAS Number: 98737-29-2
• MDL Number: MFCD02258997
• PubChem SID: 162033279; 24871318
• PubChem CID: 9903372

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: 28.766449 Å^3
• Polar Surface Area: 50.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 124-126°C; 125-127 °C(lit.)
• Optical Rotation: [α]23/D -7°, c = 0.6 in methanol

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: 95+%; 98%; 99%
• Empirical Formula (Hill Notation): C15H21NO3

DETAILS

Sigma Aldrich - 476951

Application
Building block employed in the synthesis of HIV-1 protease inhibitors.1,2
Employed in synthesizing (hydroxyethyl)urea peptidomimetrics and arylsulfonamides possessing anti-HIV activity.
Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - B618530

Atazanavir intermediate. Enantiomer S.

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 (1999)