methyl (2R,3R,4S)-4-(cyanoamino)-3-acetamido-2-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate

• ChemBase ID: 165152
• Molecular Formular: C19H25N3O10
• Molecular Mass: 455.4159
• Monoisotopic Mass: 455.15399402
• SMILES: C1=C(O[C@H]([C@@H]([C@H]1NC#N)NC(=O)C)[C@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC
• Canonical SMILES: N#CN[C@H]1C=C(O[C@H]([C@@H]1NC(=O)C)[C@H]([C@H](OC(=O)C)COC(=O)C)OC(=O)C)C(=O)OC
• InChI: InChI=1S/C19H25N3O10/c1-9(23)22-16-13(21-8-20)6-14(19(27)28-5)32-18(16)17(31-12(4)26)15(30-11(3)25)7-29-10(2)24/h6,13,15-18,21H,7H2,1-5H3,(H,22,23)/t13-,15+,16+,17-,18+/m0/s1
• InChIKey: UDLJDHWFIOYHGL-IREHDKGXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,3R,4S)-4-(cyanoamino)-3-acetamido-2-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-3,4-dihydro-2H-pyran-6-carboxylate
• IUPAC Traditional name: methyl (4S,5R,6R)-4-(cyanoamino)-5-acetamido-6-[(1R,2R)-1,2,3-tris(acetyloxy)propyl]-5,6-dihydro-4H-pyran-2-carboxylate
• Synonyms: 5-(Acetylamino)-4-(N-cyano)amino-2,6-anhydro-3,4,5-trideoxy-D-glycero-D-galacto-Non-2-enonic Acid Methyl Ester 7,8,9-Triacetate; N-Cyano Zanamivir Amine Triacetate Methyl Ester

Database IDs

• CAS Number: 1228216-82-7
• PubChem SID: 162259285
• PubChem CID: 71315059

CALCULATED PROPERTIES

• Acid pKa: 9.514151
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.6793339
• LogD (pH = 7.4): -1.6793369
• Log P: -1.6793333
• Molar Refractivity: 103.7253 cm^3
• Polarizability: 41.091995 Å^3
• Polar Surface Area: 179.35 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid

DETAILS

Toronto Research Chemicals - C987705

Intermediate in the preparation of Zanamivir.