(3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydroisoquinoline-3-carboxamide

• ChemBase ID: 160181
• Molecular Formular: C24H39N3O2
• Molecular Mass: 401.58536
• Monoisotopic Mass: 401.3042275
• SMILES: C1CC[C@H]2[C@@H](C1)C[C@H](N(C2)CC(O)[C@H](Cc1ccccc1)N)C(=O)NC(C)(C)C
• Canonical SMILES: N[C@H](C(CN1C[C@H]2CCCC[C@H]2C[C@H]1C(=O)NC(C)(C)C)O)Cc1ccccc1
• InChI: InChI=1S/C24H39N3O2/c1-24(2,3)26-23(29)21-14-18-11-7-8-12-19(18)15-27(21)16-22(28)20(25)13-17-9-5-4-6-10-17/h4-6,9-10,18-22,28H,7-8,11-16,25H2,1-3H3,(H,26,29)/t18-,19+,20-,21-,22?/m0/s1
• InChIKey: YJRJYYPXNAHNMD-INFJVKRUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-decahydroisoquinoline-3-carboxamide
• IUPAC Traditional name: (3S,4aS,8aS)-2-[(3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-tert-butyl-octahydro-1H-isoquinoline-3-carboxamide
• Synonyms: (3S,4aS,8aS)-2-[(2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl]-N-(1,1-dimethylethyl)decahydro-3-isoquinolinecarboxamide; [3S-[2(2S*,3R*),3α,4aβ,8aβ]]-2-(3-Amino-2-hydroxy-4-phenylbutyl)-N-(1,1-dimethylethyl)decahydro-3-isoquinolinecarboxamide

Database IDs

• CAS Number: 136522-17-3
• PubChem SID: 162254316
• PubChem CID: 22867602

CALCULATED PROPERTIES

• Acid pKa: 14.211154
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -2.3299441
• LogD (pH = 7.4): 0.3319508
• Log P: 2.9241543
• Molar Refractivity: 117.8546 cm^3
• Polarizability: 46.83252 Å^3
• Polar Surface Area: 78.59 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A611580

(3S,4aS,8aS)-2-[(2R,3S)-3-Amino-2-hydroxy-4-phenylbutyl]-N-(1,1-dimethylethyl)decahydro-3-isoquinolinecarboxamide is an intermediate in the synthesis of Saquinavir (S135000).

REFERENCES

• Greenwood, B., et al.: Lancet, 365, 1487 (2005)
• Andrews, K., et al.: Antimicrob. Agents Chemother., 50, 639 (2005)
• Ersmark, K., et al.: Bioorg. Med. Chem., 14, 2197 (2005)