(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(ethylsulfanyl)oxane

• ChemBase ID: 168773
• Molecular Formular: C36H40O5S
• Molecular Mass: 584.7648
• Monoisotopic Mass: 584.25964538
• SMILES: [C@@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COCc1ccccc1)SCC)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• Canonical SMILES: CCS[C@@H]1O[C@@H](COCc2ccccc2)[C@H]([C@@H]([C@@H]1OCc1ccccc1)OCc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C36H40O5S/c1-2-42-36-35(40-26-31-21-13-6-14-22-31)34(39-25-30-19-11-5-12-20-30)33(38-24-29-17-9-4-10-18-29)32(41-36)27-37-23-28-15-7-3-8-16-28/h3-22,32-36H,2,23-27H2,1H3/t32-,33-,34+,35-,36+/m1/s1
• InChIKey: NRALMNQUAKWSMF-GJXDWMKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(ethylsulfanyl)oxane
• IUPAC Traditional name: (2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-[(benzyloxy)methyl]-6-(ethylsulfanyl)oxane
• Synonyms: Ethyl 2,3,4,6-Tetrakis-O-(phenylmethyl)-1-thio-β-D-glucopyranoside; Ethyl β-Thioglucopyranoside Tetrabenzyl

Database IDs

• CAS Number: 108739-67-9
• PubChem SID: 162262905
• PubChem CID: 11017360

CALCULATED PROPERTIES

• H Acceptors: 5
• H Donor: 0
• LogD (pH = 5.5): 8.145007
• LogD (pH = 7.4): 8.145007
• Log P: 8.145007
• Molar Refractivity: 169.0478 cm^3
• Polarizability: 67.02263 Å^3
• Polar Surface Area: 46.15 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: White Solid

DETAILS

Toronto Research Chemicals - E927000

Α thioglucoside with antitumor potential.

REFERENCES

• Komba, S., et al.: Bioorg. Med. Chem., 4, 1833 (1996)
• Bertozzi, C., et al.: Science, 291, 2357 (1996)
• Davis, B., et al.: Chem. Rev., 102, 579 (1996)