[(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-(6-{[(benzyloxy)carbonyl]amino}hexanamido)-5-acetamidooxan-2-yl]methyl acetate

• ChemBase ID: 158919
• Molecular Formular: C28H39N3O11
• Molecular Mass: 593.62276
• Monoisotopic Mass: 593.25845908
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)NC(=O)CCCCCNC(=O)OCc1ccccc1)NC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: O=C(OCc1ccccc1)NCCCCCC(=O)N[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1NC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C28H39N3O11/c1-17(32)30-24-26(41-20(4)35)25(40-19(3)34)22(16-38-18(2)33)42-27(24)31-23(36)13-9-6-10-14-29-28(37)39-15-21-11-7-5-8-12-21/h5,7-8,11-12,22,24-27H,6,9-10,13-16H2,1-4H3,(H,29,37)(H,30,32)(H,31,36)/t22-,24-,25-,26-,27-/m1/s1
• InChIKey: IOPFVSXJJUSZIV-FZTDQTOTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-(6-{[(benzyloxy)carbonyl]amino}hexanamido)-5-acetamidooxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4R,5R,6R)-3,4-bis(acetyloxy)-6-(6-{[(benzyloxy)carbonyl]amino}hexanamido)-5-acetamidooxan-2-yl]methyl acetate
• Synonyms: [6-Oxo-6-[[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]amino]hexyl]carbamic Acid Phenylmethyl Ester; 2-Acetamido-3,4,6-tri-O-acetyl-N-[N-(benzyloxycarbonyl)-ε-aminocaproyl]-2-deoxy-β-D-glucopyranosylamine; 2-Acetamido-2-deoxy-3,4,6-tri-O-acetyl-N[N-(benzyloxycarbonyl)-ε-aminocaproyl]-β-D-glucopyranosylamine

Database IDs

• CAS Number: 56146-88-4
• PubChem SID: 162253054
• PubChem CID: 71312740

CALCULATED PROPERTIES

• Acid pKa: 11.5441065
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): 0.4680581
• LogD (pH = 7.4): 0.4680313
• Log P: 0.4680589
• Molar Refractivity: 143.2766 cm^3
• Polarizability: 57.653996 Å^3
• Polar Surface Area: 184.66 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: White Solid
• Melting Point: 218-219°C

DETAILS

Toronto Research Chemicals - A158382

Ligand for wheat germ agglutinin

REFERENCES

• Lis, H., et al.: Methods Enzymol., 34-Part B, 341 (1974)