(2R,3S,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(methanesulfonyloxy)hexan-2-yl methanesulfonate

• ChemBase ID: 178249
• Molecular Formular: C36H42O10S2
• Molecular Mass: 698.84268
• Monoisotopic Mass: 698.22193954
• SMILES: C([C@@H]([C@H]([C@@H]([C@@H](COCc1ccccc1)OS(=O)(=O)C)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1)OS(=O)(=O)C
• Canonical SMILES: CS(=O)(=O)O[C@@H]([C@H]([C@@H]([C@H](COS(=O)(=O)C)OCc1ccccc1)OCc1ccccc1)OCc1ccccc1)COCc1ccccc1
• InChI: InChI=1S/C36H42O10S2/c1-47(37,38)45-28-33(42-24-30-17-9-4-10-18-30)35(43-25-31-19-11-5-12-20-31)36(44-26-32-21-13-6-14-22-32)34(46-48(2,39)40)27-41-23-29-15-7-3-8-16-29/h3-22,33-36H,23-28H2,1-2H3/t33-,34+,35+,36+/m0/s1
• InChIKey: PSRQUUMTYKKBPW-NJMTUYGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(methanesulfonyloxy)hexan-2-yl methanesulfonate
• IUPAC Traditional name: (2R,3S,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(methanesulfonyloxy)hexan-2-yl methanesulfonate
• Synonyms: 2,3,4,6-Tetrakis-O-(phenylmethyl)-D-glucitol Dimethanesulfonate; 2,3,4,6-Tetra-O-benzyl-1,5-di-O-methanesulfonyl-D-glucitol

Database IDs

• CAS Number: 77698-99-8
• PubChem SID: 164234159
• PubChem CID: 11050769

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 5.612708
• LogD (pH = 7.4): 5.612708
• Log P: 5.612708
• Molar Refractivity: 181.3638 cm^3
• Polarizability: 73.718956 Å^3
• Polar Surface Area: 123.66 Å^2
• Rotatable Bonds: 21
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Methanol
• Apperance: Light Orange Liquid

Safety Information

• Storage Warning: Moisture, Temperature Sensitive

DETAILS

Toronto Research Chemicals - T284850

2,3,4,6-Tetra-O-benzyl-1,5-di-O-methanesulfonyl-D-glucitol is used in the synthesis of pharmaceutically active aza-sugar piperidine derivatives as inhibitors of galactosidase and glucosylceramide synthase.

REFERENCES

• Fowler, P.A., et al.: Carbohydr. Res., 246 377 (1993)