ethyl (3S,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

• ChemBase ID: 166049
• Molecular Formular: C14H24N4O3
• Molecular Mass: 296.36536
• Monoisotopic Mass: 296.18484065
• SMILES: [C@H]1([C@@H](CC(=C[C@@H]1OC(CC)CC)C(=O)OCC)N=[N+]=[N-])N
• Canonical SMILES: CCOC(=O)C1=C[C@H](OC(CC)CC)[C@@H]([C@@H](C1)N=[N+]=[N-])N
• InChI: InChI=1S/C14H24N4O3/c1-4-10(5-2)21-12-8-9(14(19)20-6-3)7-11(13(12)15)17-18-16/h8,10-13H,4-7,15H2,1-3H3/t11-,12-,13+/m0/s1
• InChIKey: UXJWNTIKRKKBGZ-RWMBFGLXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (3S,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: ethyl (3S,4R,5S)-4-amino-5-azido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• Synonyms: (3R,4R,5S)-4-Amino-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid Ethyl Ester; Ethyl (3R,4R,5S)-4-Amino-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate; N-Desacetyl 5-Azido Oseltamivir

Database IDs

• CAS Number: 204255-04-9
• PubChem SID: 162260182
• PubChem CID: 71315529

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.78905874
• LogD (pH = 7.4): 0.38782242
• Log P: 2.2709782
• Molar Refractivity: 79.3946 cm^3
• Polarizability: 30.823069 Å^3
• Polar Surface Area: 90.98 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Brown Oil

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D288415

Intermediate in the production of Oseltamivir.

REFERENCES

• Williams, M., et al.: Bioorg. Med. Chem. Lett., 7, 1837 (1997)