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

• ChemBase ID: 159368
• Molecular Formular: C21H31NO13
• Molecular Mass: 505.46974
• Monoisotopic Mass: 505.17954006
• SMILES: [C@@H]1([C@@H]([C@@H](C[C@@](O1)(C(=O)OC)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(OC)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/C21H31NO13/c1-10(23)22-17-15(32-12(3)25)8-21(30-7,20(28)29-6)35-19(17)18(34-14(5)27)16(33-13(4)26)9-31-11(2)24/h15-19H,8-9H2,1-7H3,(H,22,23)/t15-,16-,17+,18+,19+,21+/m0/s1
• InChIKey: BDVAGIAWBFWKLD-RLDZVTRJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2R,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-methoxy-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2R,4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-methoxy-6-[(1S,2S)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: Methyl(methyl-5-acetamido-4,7,8,9-tetra-D-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranoside)onate; N-Acetyl-2-O-methyl-α-neuraminic Acid Methyl Ester 4,7,8,9-Tetraacetate

Database IDs

• CAS Number: 73208-80-7
• PubChem SID: 162253503
• PubChem CID: 12897692

CALCULATED PROPERTIES

• Acid pKa: 12.846
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -1.0104159
• LogD (pH = 7.4): -1.0104167
• Log P: -1.0104153
• Molar Refractivity: 109.9077 cm^3
• Polarizability: 45.57383 Å^3
• Polar Surface Area: 179.06 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ether; Ethyl Acetate
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A186720

Intermediate for the synthesis of supressor T cell inducers.

REFERENCES

• Kijima, I., et al.: Chem. Pharm. Bull., 30, 3278 (1982)
• Knibbs, R.N., et al.: J. Biol. Chem., 268, 18524 (1982)