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

• ChemBase ID: 131867
• Molecular Formular: C21H31NO12S
• Molecular Mass: 521.53534
• Monoisotopic Mass: 521.15669644
• SMILES: CC(=O)N[C@@H]1[C@H](CC(O[C@H]1[C@@H]([C@@H](COC(=O)C)OC(=O)C)OC(=O)C)(C(=O)OC)SC)OC(=O)C
• Canonical SMILES: COC(=O)C1(SC)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/C21H31NO12S/c1-10(23)22-17-15(31-12(3)25)8-21(35-7,20(28)29-6)34-19(17)18(33-14(5)27)16(32-13(4)26)9-30-11(2)24/h15-19H,8-9H2,1-7H3,(H,22,23)/t15-,16+,17+,18+,19+,21?/m0/s1
• InChIKey: VUDPJAWMOISBAC-KUHALTKMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-(methylsulfanyl)-6-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• IUPAC Traditional name: methyl (4S,5R,6R)-4-(acetyloxy)-5-acetamido-2-(methylsulfanyl)-6-[(1S,2R)-1,2,3-tris(acetyloxy)propyl]oxane-2-carboxylate
• Synonyms: Methyl 4,7,8,9-tetra-O-acetyl-2-thio-N-acetyl-α-D-neuraminic acid methyl ester

Database IDs

• CAS Number: 116450-06-7
• MDL Number: MFCD00792863
• PubChem SID: 162226144
• PubChem CID: 11731041

CALCULATED PROPERTIES

• Acid pKa: 12.878475
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): -0.22271973
• LogD (pH = 7.4): -0.22272043
• Log P: -0.22271915
• Molar Refractivity: 115.9345 cm^3
• Polarizability: 47.87898 Å^3
• Polar Surface Area: 169.83 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-46-23/24/25-36/37/38
• Safety Statements: 53-23-26-36/37/39-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H311-H315-H319-H331-H335-H350
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - M8797

Application
N-Acetylneuraminic acid derivative (glycosyl donor) suitable for chemical sialylation of carbohydrates.