dibenzyl [(2R,4R,5S)-5-({[bis(benzyloxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate

• ChemBase ID: 160670
• Molecular Formular: C34H38O11P2
• Molecular Mass: 684.606442
• Monoisotopic Mass: 684.1889353
• SMILES: [C@@H]1(C([C@H](O[C@H]1COP(=O)(OCc1ccccc1)OCc1ccccc1)COP(=O)(OCc1ccccc1)OCc1ccccc1)O)O
• Canonical SMILES: OC1[C@@H](COP(=O)(OCc2ccccc2)OCc2ccccc2)O[C@H]([C@H]1O)COP(=O)(OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C34H38O11P2/c35-33-31(25-43-46(37,39-21-27-13-5-1-6-14-27)40-22-28-15-7-2-8-16-28)45-32(34(33)36)26-44-47(38,41-23-29-17-9-3-10-18-29)42-24-30-19-11-4-12-20-30/h1-20,31-36H,21-26H2/t31-,32+,33-,34?/m0/s1
• InChIKey: WDFLDGLHRHVJCE-UYHYCKRPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: dibenzyl [(2R,4R,5S)-5-({[bis(benzyloxy)phosphoryl]oxy}methyl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• IUPAC Traditional name: dibenzyl [(2R,4R,5S)-5-{[(dibenzyloxyphosphoryl)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]methyl phosphate
• Synonyms: 2,5-Anhydro-D-glucitol-1,6-bis-(dibenzylphosphate)

Database IDs

• PubChem SID: 162254805
• PubChem CID: 57369140

CALCULATED PROPERTIES

• Acid pKa: 12.764022
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 5.594288
• LogD (pH = 7.4): 5.594286
• Log P: 5.594288
• Molar Refractivity: 173.0189 cm^3
• Polarizability: 69.50421 Å^3
• Polar Surface Area: 139.21 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Syrup

REFERENCES

• Koerner Jr., T.A.W. et al.: JBC 249(18)
• 5749-5754 (18)
• Reitz, A.B. et al.: Tetrahedron Letters, 26(18)
• 3915-3918 (1985)