methyl (2R,4S,5R,6R)-4-(acetyloxy)-2-chloro-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate

• ChemBase ID: 159141
• Molecular Formular: C20H28ClNO12
• Molecular Mass: 509.88882
• Monoisotopic Mass: 509.13000302
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(Cl)C(=O)OC)OC(=O)C)NC(=O)C)[C@@H]([C@H](COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: COC(=O)[C@]1(Cl)C[C@@H](OC(=O)C)[C@H]([C@@H](O1)[C@@H]([C@@H](OC(=O)C)COC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C20H28ClNO12/c1-9(23)22-16-14(31-11(3)25)7-20(21,19(28)29-6)34-18(16)17(33-13(5)27)15(32-12(4)26)8-30-10(2)24/h14-18H,7-8H2,1-6H3,(H,22,23)/t14-,15-,16+,17+,18+,20-/m0/s1
• InChIKey: QGJGGAMXXWIKJR-ZGRIBIJBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,4S,5R,6R)-4-(acetyloxy)-2-chloro-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,4S,5R,6R)-4-(acetyloxy)-2-chloro-5-acetamido-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: N-Acetyl-2-chloro-2-deoxy-β-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate; 5-(Acetylamino)-2-chloro-2,3,5-trideoxy-D-glycero-β-D-galacto-2-nonulopyranosonic Acid Methyl Ester 4,7,8,9-Tetraacetate; N-Acetyl-2-chloro-2-deoxy-β-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

Database IDs

• CAS Number: 67670-69-3
• PubChem SID: 162253276
• PubChem CID: 13146314

CALCULATED PROPERTIES

• Acid pKa: 12.37027
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.45978442
• LogD (pH = 7.4): -0.4597879
• Log P: -0.4597838
• Molar Refractivity: 108.6941 cm^3
• Polarizability: 44.93678 Å^3
• Polar Surface Area: 169.83 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 104-106°C

DETAILS

Toronto Research Chemicals - A168405

Intermediate in the preparation of neuraminic acid derivatives

REFERENCES

• Tindal, D., et al.: Bioorg. Med. Chem. Lett., 17, 1655 (2007)