benzyl N-[(4R,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate

• ChemBase ID: 163648
• Molecular Formular: C14H19NO7
• Molecular Mass: 313.30316
• Monoisotopic Mass: 313.11615195
• SMILES: [C@@H]1([C@@H](C(C(OC1CO)O)NC(=O)OCc1ccccc1)O)O
• Canonical SMILES: OCC1OC(O)C([C@H]([C@@H]1O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C14H19NO7/c16-6-9-11(17)12(18)10(13(19)22-9)15-14(20)21-7-8-4-2-1-3-5-8/h1-5,9-13,16-19H,6-7H2,(H,15,20)/t9?,10?,11-,12-,13?/m1/s1
• InChIKey: FRTOTMQAWIIMKK-JBSNKVJHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-[(4R,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate
• IUPAC Traditional name: benzyl N-[(4R,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]carbamate
• Synonyms: 2-Deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-mannose; N-Carbobenzyloxy Mannosamine; 2-Deoxy-2-[[(phenylmethoxy)carbonyl]amino]-D-glucose; N-Carbobenzyloxy-D-glucosamine; NSC 170196; NCBZG; 2-N-Carbobenzyloxy-2-deoxy-D-glucosamine

Database IDs

• CAS Number: 16684-31-4; 137157-50-7
• PubChem SID: 162257783
• PubChem CID: 46780169

CALCULATED PROPERTIES

• Acid pKa: 11.684579
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -0.87681043
• LogD (pH = 7.4): -0.8768326
• Log P: -0.87681013
• Molar Refractivity: 73.2609 cm^3
• Polarizability: 29.572517 Å^3
• Polar Surface Area: 128.48 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White Solid
• Melting Point: 209-211°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C176500

A synthetic sugar analog with antiviral activity.

REFERENCES

• Halperen, S., et al.: J. Gen. Virology, 33, 389 (1976)