ethyl (4R,5S)-5-azido-4-(2H3)acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

• ChemBase ID: 161071
• Molecular Formular: C16H26N4O4
• Molecular Mass: 338.40204
• Monoisotopic Mass: 338.19540533
• SMILES: [C@H]1([C@@H](CC(=CC1OC(CC)CC)C(=O)OCC)N=[N+]=[N-])NC(=O)C
• Canonical SMILES: CCOC(=O)C1=CC(OC(CC)CC)[C@@H]([C@@H](C1)N=[N+]=[N-])NC(=O)C
• InChI: InChI=1S/C16H26N4O4/c1-5-12(6-2)24-14-9-11(16(22)23-7-3)8-13(19-20-17)15(14)18-10(4)21/h9,12-15H,5-8H2,1-4H3,(H,18,21)/t13-,14?,15+/m0/s1
• InChIKey: MPTCBJSPQVJIPZ-ZHDDOTHNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (4R,5S)-5-azido-4-(^2H₃)acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: ethyl (4R,5S)-5-azido-4-(^2H₃)acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• Synonyms: [3R-(3α,4β,5α)]-4-(Acetylamino)-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid-d3 Ethyl Ester; (3R,4R,5S)-4-(Acetylamino)-5-azido-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic Acid-d3 Ethyl Ester; 5-Azido Oseltamivir-d3

Database IDs

• PubChem SID: 162255206
• PubChem CID: 71313600

CALCULATED PROPERTIES

• Acid pKa: 13.584083
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 1.9757785
• LogD (pH = 7.4): 1.9757788
• Log P: 2.0898247
• Molar Refractivity: 88.8384 cm^3
• Polarizability: 34.228733 Å^3
• Polar Surface Area: 94.06 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - A919962

Intermediate in the production of Oseltamivir.

REFERENCES

• Kim, C., et al.: J. Med. Chem., 41, 2451 (1998)
• Carbain, B., et al.: Chem. Med. Chem., 4, 335 (1998)