[(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxan-2-yl]methyl acetate

• ChemBase ID: 175225
• Molecular Formular: C21H25NO11S
• Molecular Mass: 499.4883
• Monoisotopic Mass: 499.11483163
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1COC(=O)C)SCc1ccc(cc1)[N+](=O)[O-])OC(=O)C)OC(=O)C)OC(=O)C
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@@H](SCc2ccc(cc2)[N+](=O)[O-])[C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C21H25NO11S/c1-11(23)29-9-17-18(30-12(2)24)19(31-13(3)25)20(32-14(4)26)21(33-17)34-10-15-5-7-16(8-6-15)22(27)28/h5-8,17-21H,9-10H2,1-4H3/t17-,18+,19+,20-,21+/m1/s1
• InChIKey: ZHFJYPUDGFUYCK-IFLJBQAJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxan-2-yl]methyl acetate
• IUPAC Traditional name: [(2R,3S,4S,5R,6S)-3,4,5-tris(acetyloxy)-6-{[(4-nitrophenyl)methyl]sulfanyl}oxan-2-yl]methyl acetate
• Synonyms: (4-Nitrophenyl)methyl 1-Thio-β-D-Galactopyranoside 2,3,4,6-Tetraacetate; 4-Nitrobenzyl 2,3,4,6-Tetra-O-acetyl-1-thio-β-D-galactopryranoside

Database IDs

• CAS Number: 35785-42-3
• PubChem SID: 164231135
• PubChem CID: 11477539

CALCULATED PROPERTIES

• H Acceptors: 7
• H Donor: 0
• LogD (pH = 5.5): 1.7467595
• LogD (pH = 7.4): 1.7467595
• Log P: 1.7467595
• Molar Refractivity: 115.3873 cm^3
• Polarizability: 46.214607 Å^3
• Polar Surface Area: 160.25 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White-Yellowish Solid
• Melting Point: 84-86°C

DETAILS

Toronto Research Chemicals - N495670

Used in the synthesis of 1-thio-β-D-glycopyranosides.

REFERENCES

• Claeyssens, M., et al.: Carbohydrate Res., 22, 460 (1972)