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

• ChemBase ID: 161023
• Molecular Formular: C30H50N6O12S2
• Molecular Mass: 750.881
• Monoisotopic Mass: 750.29281307
• SMILES: [C@H]1([C@@H](CC(=C[C@@H]1OC(CC)CC)C(=O)OCC)N=[N+]=[N-])OS(=O)(=O)C.[C@H]1([C@@H](CC(=C[C@@H]1OC(CC)CC)C(=O)OCC)OS(=O)(=O)C)N=[N+]=[N-]
• Canonical SMILES: [N-]=[N+]=N[C@H]1[C@@H](OC(CC)CC)C=C(C[C@H]1OS(=O)(=O)C)C(=O)OCC.[N-]=[N+]=N[C@@H]1CC(=C[C@@H]([C@@H]1OS(=O)(=O)C)OC(CC)CC)C(=O)OCC
• InChI: InChI=1S/2C15H25N3O6S/c1-5-11(6-2)23-12-8-10(15(19)22-7-3)9-13(14(12)17-18-16)24-25(4,20)21;1-5-11(6-2)23-13-9-10(15(19)22-7-3)8-12(17-18-16)14(13)24-25(4,20)21/h8,11-14H,5-7,9H2,1-4H3;9,11-14H,5-8H2,1-4H3/t12-,13-,14-;12-,13-,14+/m00/s1
• InChIKey: WXMIEYILIDSUPR-HUUYPTBLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (3S,4R,5S)-5-azido-4-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate ethyl (3S,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• IUPAC Traditional name: ethyl (3S,4R,5S)-5-azido-4-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate ethyl (3S,4S,5S)-4-azido-5-(methanesulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate
• Synonyms: Ethyl (3R,4S,5S)-4-Azido-3-(1-ethylpropoxy)-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-Carboxylate + Ethyl (3R,4S,5S)-5-Azido-3-(1-ethylpropoxy)-4-[(methylsulfonyl)oxy]-1-cyclohexene-1-Carboxylate (Mixture of Isomers); (3R,4S,5S)-4-Azido-3-(1-ethylpropoxy)-5-[(methylsulfonyl)oxy]-1-cyclohexene-1-Carboxylic Acid Ethyl Ester + (3R,4S,5S)-5-Azido-3-(1-ethylpropoxy)-4-[(methylsulfonyl)oxy]-1-cyclohexene-1-Carboxylic Acid Ethyl Ester (Mixture of Isomers)

Database IDs

• PubChem SID: 162255158
• PubChem CID: 71313585

CALCULATED PROPERTIES

• Acid pKa: 18.259789
• H Acceptors: 6
• H Donor: 0
• LogD (pH = 5.5): 2.1999786
• LogD (pH = 7.4): 2.1999786
• Log P: 2.3140242
• Molar Refractivity: 90.4896 cm^3
• Polarizability: 36.1386 Å^3
• Polar Surface Area: 108.33 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate; Methanol
• Apperance: Light Brown Oil

DETAILS

Toronto Research Chemicals - A848985

Mixture of isomers used in the preparation of Oseltamivir.

REFERENCES

• Enserink, M., et al.: Science, 312, 382 (2006)