[(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R,6S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(4-aminophenyl)sulfanyl]oxan-3-yl]oxy}oxan-2-yl]methyl acetate

• ChemBase ID: 160430
• Molecular Formular: C32H41NO17S
• Molecular Mass: 743.72944
• Monoisotopic Mass: 743.20951986
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)O[C@H]1[C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)Sc1ccc(cc1)N)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](Sc2ccc(cc2)N)[C@H]([C@H]([C@@H]1O[C@@H]1O[C@@H](COC(=O)C)[C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C32H41NO17S/c1-14(34)41-12-23-25(43-16(3)36)27(44-17(4)37)29(46-19(6)39)31(48-23)50-26-24(13-42-15(2)35)49-32(51-22-10-8-21(33)9-11-22)30(47-20(7)40)28(26)45-18(5)38/h8-11,23-32H,12-13,33H2,1-7H3/t23-,24-,25-,26-,27+,28+,29-,30-,31+,32+/m1/s1
• InChIKey: MZPWTWYHBZEZSN-CBUXPLGESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R,6S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(4-aminophenyl)sulfanyl]oxan-3-yl]oxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R,6S)-4,5-bis(acetyloxy)-2-[(acetyloxy)methyl]-6-[(4-aminophenyl)sulfanyl]oxan-3-yl]oxy}oxan-2-yl]methyl acetate
• Synonyms: 4-Aminophenyl 2,3,6-Tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside

Database IDs

• CAS Number: 68636-50-0
• PubChem SID: 162254565
• PubChem CID: 54099602

CALCULATED PROPERTIES

• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): 0.27336106
• LogD (pH = 7.4): 0.28739628
• Log P: 0.28757823
• Molar Refractivity: 167.8942 cm^3
• Polarizability: 68.864395 Å^3
• Polar Surface Area: 237.81 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 174-176°C

DETAILS

Toronto Research Chemicals - A627325

Shown to be a functional affinity ligand for the separation of exo-(cellobiohydrolasees) and endo-(endoglucanases) acting cellulases.

REFERENCES

• Piyachomkwan, K., et al.: Carbohydrate Research, 303, 255 (1997)