benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate

• ChemBase ID: 163848
• Molecular Formular: C32H45N3O4S
• Molecular Mass: 567.7824
• Monoisotopic Mass: 567.31307794
• SMILES: c1cccc(c1)COC(=O)N[C@H]([C@@H](CN1C[C@@H]2[C@H](C[C@H]1C(=O)NC(C)(C)C)CCCC2)O)CSc1ccccc1
• Canonical SMILES: O=C(N[C@H]([C@@H](CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)O)CSc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C32H45N3O4S/c1-32(2,3)34-30(37)28-18-24-14-10-11-15-25(24)19-35(28)20-29(36)27(22-40-26-16-8-5-9-17-26)33-31(38)39-21-23-12-6-4-7-13-23/h4-9,12-13,16-17,24-25,27-29,36H,10-11,14-15,18-22H2,1-3H3,(H,33,38)(H,34,37)/t24-,25+,27-,28-,29+/m0/s1
• InChIKey: CADGDESSNWSRRZ-RIVMDFSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-decahydroisoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate
• IUPAC Traditional name: benzyl N-[(2R,3R)-4-[(3S,4aS,8aS)-3-(tert-butylcarbamoyl)-octahydro-1H-isoquinolin-2-yl]-3-hydroxy-1-(phenylsulfanyl)butan-2-yl]carbamate
• Synonyms: [(1R,2R)-3-[(3S,4aS,8aS)-3-[[(1,1-Dimethylethyl)amino]carbonyl]octahydro-2(1H)-isoquinolinyl]-2-hydroxy-1-[(phenylthio)methyl]propyl]carbamic Acid Phenylmethyl Ester; [3S-(3S,4aS,8aS,2'R,3'R)]-2-[3'-N-CBz-amino-2'-hydroxy-4'-(phenyl)thio]butyldecahydroisoquinoline-3-N-t-butylcarboxamide

Database IDs

• CAS Number: 159878-04-3
• PubChem SID: 162257983
• PubChem CID: 10962812

CALCULATED PROPERTIES

• Acid pKa: 13.866607
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.6598432
• LogD (pH = 7.4): 4.432956
• Log P: 5.2438836
• Molar Refractivity: 161.2181 cm^3
• Polarizability: 63.593315 Å^3
• Polar Surface Area: 90.9 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichlormethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 130-134°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C210000

An intermediate in the synthesis of Nelfinavir.

REFERENCES

• Kaldor, S., et al.: J. Med. Chem., 40, 3979 (1997)