[(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate

• ChemBase ID: 131753
• Molecular Formular: C16H23NO10
• Molecular Mass: 389.35452
• Monoisotopic Mass: 389.13219594
• SMILES: CC(=O)N[C@@H]1[C@H]([C@@H]([C@H](O[C@H]1OC(=O)C)COC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@H]1O[C@@H](OC(=O)C)[C@@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C16H23NO10/c1-7(18)17-13-15(25-10(4)21)14(24-9(3)20)12(6-23-8(2)19)27-16(13)26-11(5)22/h12-16H,6H2,1-5H3,(H,17,18)/t12-,13-,14-,15-,16-/m1/s1
• InChIKey: OVPIZHVSWNOZMN-OXGONZEZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6S)-3,4,6-tris(acetyloxy)-5-acetamidooxan-2-yl]methyl acetate
• Synonyms: 2-Amino-2-deoxy-β-D-glucopyranosyl pentaacetate; β-D-Glucosamine pentaacetate; β-D-Glucosamine pentaacetate; 2-Acetamido-2-deoxy-β-D-glucopyranose 1,3,4,6-tetraacetate; 2-(Acetylamino)-2-deoxy-β-D-Glucopyranose 1,3,4,6-Tetraacetate; 1,3,4,6-Tetra-O-acetyl-N-acetyl-β-D-glucosamine; N-Acetyl-β-D-glucosamine Tetraacetate; NSC 224432; β-D-Glucosamine Pentaacetate; β-D-葡萄糖胺五乙酸酯; 2-氨基-2-脱氧-β-D-葡萄糖五乙酸酯; 2-乙酰氨基-1,3,4,6-四-O-乙酰基-2-脱氧-β-D-吡喃葡萄糖

Database IDs

• CAS Number: 7772-79-4
• EC Number: 231-865-4
• MDL Number: MFCD00006595
• PubChem SID: 162226030; 24888495
• PubChem CID: 99461

CALCULATED PROPERTIES

• Acid pKa: 12.145199
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -1.456073
• LogD (pH = 7.4): -1.4560797
• Log P: -1.4560728
• Molar Refractivity: 83.6307 cm^3
• Polarizability: 34.8191 Å^3
• Polar Surface Area: 143.53 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid
• Melting Point: 186-189 °C(lit.); 187-189°C
• Optical Rotation: [α]24/D +1.7 to +3.0°, c = 10 in chloroform

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: 98%
• Empirical Formula (Hill Notation): C16H23NO10

DETAILS

Sigma Aldrich - 859990

Packaging
1, 5 g in glass bottle

Toronto Research Chemicals - G515000

An N-acetylglucosamine derivatives as promoters for hyaluronic acid production.

REFERENCES

• Bastida, A., et al.: Biotechnol. Bioeng., 58, 486 (1998)
• Mong, T., et al.: Chem. Biochem., 4, 835 (1998)
• Mogensen, J., et al.: Biochemistry, 44, 1719 (1998)