[(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R)-3,4,5-tris(acetyloxy)-6-hydroxyoxan-2-yl]methoxy}oxan-2-yl]methyl acetate

• ChemBase ID: 178210
• Molecular Formular: C26H36O18
• Molecular Mass: 636.55324
• Monoisotopic Mass: 636.19016431
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)OC[C@H]1[C@H]([C@@H]([C@@H](C(O1)O)OC(=O)C)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](OC[C@@H]2OC(O)[C@H]([C@H]([C@@H]2OC(=O)C)OC(=O)C)OC(=O)C)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C26H36O18/c1-10(27)35-8-18-20(38-12(3)29)22(40-14(5)31)24(42-16(7)33)26(44-18)36-9-17-19(37-11(2)28)21(39-13(4)30)23(25(34)43-17)41-15(6)32/h17-26,34H,8-9H2,1-7H3/t17-,18-,19-,20-,21+,22+,23-,24-,25?,26-/m1/s1
• InChIKey: SPWFGEAKPYYJQD-XDSCNRSSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R)-3,4,5-tris(acetyloxy)-6-hydroxyoxan-2-yl]methoxy}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3R,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-{[(2R,3R,4S,5R)-3,4,5-tris(acetyloxy)-6-hydroxyoxan-2-yl]methoxy}oxan-2-yl]methyl acetate
• Synonyms: 6-O-(2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-D-glucose 2,3,4-Triacetate

Database IDs

• CAS Number: 56253-33-9
• PubChem SID: 164234120
• PubChem CID: 71752389

CALCULATED PROPERTIES

• Acid pKa: 11.3185
• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): -1.6154977
• LogD (pH = 7.4): -1.6155493
• Log P: -1.615497
• Molar Refractivity: 132.3972 cm^3
• Polarizability: 55.93843 Å^3
• Polar Surface Area: 232.02 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T280450

It is used in the synthesis of diverse analogs of Amygdalin as potential peptidomimetics of peptide T.

REFERENCES

• Llorens, O., et al.: Bioorg. Med. Chem. Lett., 8, 781 (1998)
• Araya, E., et al.: Bioorg. Med. Chem. Lett., 15, 1493 (1998)