(3R,4S)-3-(acetyloxy)-4-(benzyloxy)-5,5-bis[(methanesulfonyloxy)methyl]oxolan-2-yl acetate

• ChemBase ID: 166938
• Molecular Formular: C19H26O12S2
• Molecular Mass: 510.53254
• Monoisotopic Mass: 510.08656827
• SMILES: [C@H]1(C(COS(=O)(=O)C)(OC([C@@H]1OC(=O)C)OC(=O)C)COS(=O)(=O)C)OCc1ccccc1
• Canonical SMILES: CC(=O)O[C@H]1C(OC(=O)C)OC([C@H]1OCc1ccccc1)(COS(=O)(=O)C)COS(=O)(=O)C
• InChI: InChI=1S/C19H26O12S2/c1-13(20)29-16-17(26-10-15-8-6-5-7-9-15)19(11-27-32(3,22)23,12-28-33(4,24)25)31-18(16)30-14(2)21/h5-9,16-18H,10-12H2,1-4H3/t16-,17+,18?/m1/s1
• InChIKey: ZEVFGCXHAWLZAT-DVKDBIPTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S)-3-(acetyloxy)-4-(benzyloxy)-5,5-bis[(methanesulfonyloxy)methyl]oxolan-2-yl acetate
• IUPAC Traditional name: (3R,4S)-3-(acetyloxy)-4-(benzyloxy)-5,5-bis[(methanesulfonyloxy)methyl]oxolan-2-yl acetate
• Synonyms: 1,2-Di-O-acetyl-3-O-benzyl-4-C-methanesulfonoxymethyl-5-O-methanesulfonyl-D-ribofuranose; 1,2-Diacetate-4-C-[[(methylsulfonyl)oxy]methyl]-3-O-(phenylmethyl)-D-erythro-pentofuranose 5-Methanesulfonate; 1,2-Di-O-acetyl-3-O-benzyl-4-C-mesylmethyl-5-O-mesyl-D-ribofuranose

Database IDs

• PubChem SID: 162261071
• PubChem CID: 10973257

CALCULATED PROPERTIES

• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 0.05364131
• LogD (pH = 7.4): 0.05364131
• Log P: 0.05364131
• Molar Refractivity: 109.3146 cm^3
• Polarizability: 46.56275 Å^3
• Polar Surface Area: 157.8 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D422460

Used in the preparation of locked nucleosides as adenosine receptor antagonists.

REFERENCES

• Gallo-Rodriguez, C., et al.: J. Med. Chem., 37,636 (1994)