(3S)-(2,2,5,5-2H4)oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-nitrobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate

• ChemBase ID: 175376
• Molecular Formular: C25H33N3O8S
• Molecular Mass: 535.60982
• Monoisotopic Mass: 535.19883603
• SMILES: C1C[C@@H](CO1)OC(=O)N[C@H]([C@@H](CN(S(=O)(=O)c1ccc(cc1)[N+](=O)[O-])CC(C)C)O)Cc1ccccc1
• Canonical SMILES: CC(CN(S(=O)(=O)c1ccc(cc1)[N+](=O)[O-])C[C@H]([C@H](Cc1ccccc1)NC(=O)O[C@@H]1COCC1)O)C
• InChI: InChI=1S/C25H33N3O8S/c1-18(2)15-27(37(33,34)22-10-8-20(9-11-22)28(31)32)16-24(29)23(14-19-6-4-3-5-7-19)26-25(30)36-21-12-13-35-17-21/h3-11,18,21,23-24,29H,12-17H2,1-2H3,(H,26,30)/t21-,23-,24+/m0/s1
• InChIKey: ZMNCIAGFQBUWTJ-OEMFJLHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-(2,2,5,5-^2H₄)oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-nitrobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• IUPAC Traditional name: (3S)-(2,2,5,5-^2H₄)oxolan-3-yl N-[(2S,3R)-3-hydroxy-4-[N-(2-methylpropyl)4-nitrobenzenesulfonamido]-1-phenylbutan-2-yl]carbamate
• Synonyms: [(1S,2R)-3-[[(4-Nitrophenyl)sulfonyl](2-methylpropyl)amino]-2-hydroxy-1-phenylmethyl)propyl]carbamic Acid, (3S)-Tetrahydro-3-furan-d4-yl Ester

Database IDs

• PubChem SID: 164231286
• PubChem CID: 45040089

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 3.1958628
• LogD (pH = 7.4): 3.1958623
• Log P: 3.1958628
• Molar Refractivity: 136.7058 cm^3
• Polarizability: 53.588394 Å^3
• Polar Surface Area: 150.99 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false
• Acid pKa: 13.380468

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - N505077

A Labelled intermediate in the synthesis of Amprenavir, a selective HIV protease inhibitor.