(2S,4S,5S)-4-amino-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,5-diol

• ChemBase ID: 161397
• Molecular Formular: C13H19NO5
• Molecular Mass: 269.29366
• Monoisotopic Mass: 269.12632271
• SMILES: [C@@H]1([C@@H](C([C@H](OC1CO)OCc1ccccc1)O)N)O
• Canonical SMILES: OCC1O[C@H](OCc2ccccc2)C([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C13H19NO5/c14-10-11(16)9(6-15)19-13(12(10)17)18-7-8-4-2-1-3-5-8/h1-5,9-13,15-17H,6-7,14H2/t9?,10-,11+,12?,13-/m0/s1
• InChIKey: QXJRFJWFMMVPGX-ZYLJPLBTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,5S)-4-amino-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,5-diol
• IUPAC Traditional name: (2S,4S,5S)-4-amino-2-(benzyloxy)-6-(hydroxymethyl)oxane-3,5-diol
• Synonyms: Phenylmethyl 3-Amino-3-deoxy-α-D-mannopyranoside Hydrochloride; Benzyl 3-Amino-3-deoxy-α-D-mannopyranoside Hydrochloride

Database IDs

• CAS Number: 172838-30-1
• PubChem SID: 162255532
• PubChem CID: 46780701

CALCULATED PROPERTIES

• Acid pKa: 12.673796
• H Acceptors: 6
• H Donor: 4
• LogD (pH = 5.5): -3.5218294
• LogD (pH = 7.4): -2.0908542
• Log P: -0.6718214
• Molar Refractivity: 66.9447 cm^3
• Polarizability: 27.306385 Å^3
• Polar Surface Area: 105.17 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 212-215°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B225000

Used for preparation of swainsonine analogs as immunostimulants.

REFERENCES

• Dime, D., et al.: PCT Int. Appl., 74 pp. (1993)