(2R,3S,4S,5R,6R)-4,5-bis(benzoyloxy)-6-[(benzoyloxy)methyl]-2-[(trichloroethanimidoyl)oxy]oxan-3-yl benzoate

• ChemBase ID: 178245
• Molecular Formular: C36H28Cl3NO10
• Molecular Mass: 740.96722
• Monoisotopic Mass: 739.07787914
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1COC(=O)c1ccccc1)OC(=N)C(Cl)(Cl)Cl)OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=O)c1ccccc1
• Canonical SMILES: O=C(c1ccccc1)O[C@@H]1[C@H](COC(=O)c2ccccc2)O[C@@H]([C@H]([C@H]1OC(=O)c1ccccc1)OC(=O)c1ccccc1)OC(=N)C(Cl)(Cl)Cl
• InChI: InChI=1S/C36H28Cl3NO10/c37-36(38,39)35(40)50-34-29(49-33(44)25-19-11-4-12-20-25)28(48-32(43)24-17-9-3-10-18-24)27(47-31(42)23-15-7-2-8-16-23)26(46-34)21-45-30(41)22-13-5-1-6-14-22/h1-20,26-29,34,40H,21H2/t26-,27-,28+,29+,34-/m1/s1
• InChIKey: KTHFOWIANASXOK-LSPAEZJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-4,5-bis(benzoyloxy)-6-[(benzoyloxy)methyl]-2-[(trichloroethanimidoyl)oxy]oxan-3-yl benzoate
• IUPAC Traditional name: (2R,3S,4S,5R,6R)-4,5-bis(benzoyloxy)-6-[(benzoyloxy)methyl]-2-[(trichloroethanimidoyl)oxy]oxan-3-yl benzoate
• Synonyms: 2,3,4,6-Tetrabenzoate α-D-Mannopyranose 1-(2,2,2-Trichloroethanimidate); 2,3,4,6-Tetra-O-benzoyl-α-D-mannopyranosyl Trichloroacetimidate

Database IDs

• CAS Number: 183901-63-5
• PubChem SID: 164234155
• PubChem CID: 10963703

CALCULATED PROPERTIES

• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 9.219254
• LogD (pH = 7.4): 9.221737
• Log P: 9.221769
• Molar Refractivity: 192.6184 cm^3
• Polarizability: 71.228966 Å^3
• Polar Surface Area: 147.51 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - T284205

Used for the preparation of mannosyl based dendrons for use as inhibitors treating microbial infections.

REFERENCES

• Rojo, J., et al.: J. Antimicrob. Chem., 54, 579 (2004)