(2R,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

• ChemBase ID: 173885
• Molecular Formular: C13H24O11
• Molecular Mass: 356.32306
• Monoisotopic Mass: 356.13186159
• SMILES: [C@@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO)OC)O)O[C@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)CO)O
• Canonical SMILES: CO[C@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O[C@H]1O[C@@H](CO)[C@H]([C@@H]([C@@H]1O)O)O)O
• InChI: InChI=1S/C13H24O11/c1-21-12-10(20)11(7(17)5(3-15)22-12)24-13-9(19)8(18)6(16)4(2-14)23-13/h4-20H,2-3H2,1H3/t4-,5-,6-,7-,8+,9+,10+,11+,12+,13-/m1/s1
• InChIKey: WOKXHOIRHHAHDA-ZEEOCKJESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• IUPAC Traditional name: (2R,3S,4S,5S,6R)-2-{[(2R,3R,4S,5S,6S)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol
• Synonyms: Man1-α-3Man-α-OMe; Methyl 3-O-(α-D-Mannopyranosyl)-α-D-mannopyranoside

Database IDs

• CAS Number: 72028-62-7
• PubChem SID: 164229795
• PubChem CID: 3080923

CALCULATED PROPERTIES

• Acid pKa: 11.940494
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -4.0602484
• LogD (pH = 7.4): -4.060261
• Log P: -4.0602484
• Molar Refractivity: 73.0879 cm^3
• Polarizability: 30.830313 Å^3
• Polar Surface Area: 178.53 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 169-174°C

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere
• Storage Warning: Hygroscopic

DETAILS

Toronto Research Chemicals - M320000

Useful in the study of UDP-N-Acetylglucosamine: a-D-mannoside β-2-N- acetylglucosaminyltransferase.

REFERENCES

• Carb. Res., 103, 15 (1982)
• Vella, G.J., et al.: Can. J. Biochem. Cell Biol., 62, 409 (1984)