(3S,4S,6S)-2-(hydroxymethyl)-6-(prop-2-en-1-yloxy)oxane-3,4,5-triol

• ChemBase ID: 159688
• Molecular Formular: C9H16O6
• Molecular Mass: 220.21974
• Monoisotopic Mass: 220.09468823
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)OCC=C)O)O)O
• Canonical SMILES: C=CCO[C@H]1OC(CO)[C@H]([C@@H](C1O)O)O
• InChI: InChI=1S/C9H16O6/c1-2-3-14-9-8(13)7(12)6(11)5(4-10)15-9/h2,5-13H,1,3-4H2/t5?,6-,7+,8?,9+/m1/s1
• InChIKey: XJNKZTHFPGIJNS-IPVXCSAOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,4S,6S)-2-(hydroxymethyl)-6-(prop-2-en-1-yloxy)oxane-3,4,5-triol
• IUPAC Traditional name: (3S,4S,6S)-2-(hydroxymethyl)-6-(prop-2-en-1-yloxy)oxane-3,4,5-triol
• Synonyms: 2-Propen-1-yl α-D-Glucopyranoside; α-D-Glucose Monoallyl Ether; Allyl α-D-Glucopyranoside

Database IDs

• CAS Number: 7464-56-4
• PubChem SID: 162253823
• PubChem CID: 46780124

CALCULATED PROPERTIES

• Acid pKa: 12.210525
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -1.5581629
• LogD (pH = 7.4): -1.5581696
• Log P: -1.5581629
• Molar Refractivity: 49.8373 cm^3
• Polarizability: 20.377367 Å^3
• Polar Surface Area: 99.38 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 92-101°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A555250

A useful synthetic intermediate for oligosaccharide synthesis.

REFERENCES

• Lee, R., et al.: J. Biol. Chem., 266, 4810 (1991)