benzyl N-(5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]carbamoyl}pentyl)carbamate

• ChemBase ID: 161695
• Molecular Formular: C20H30N2O7
• Molecular Mass: 410.4614
• Monoisotopic Mass: 410.20530131
• SMILES: C1([C@H]([C@H](C([C@H](O1)NC(=O)CCCCCNC(=O)OCc1ccccc1)O)O)O)C
• Canonical SMILES: O=C(OCc1ccccc1)NCCCCCC(=O)N[C@H]1OC(C)[C@H]([C@H](C1O)O)O
• InChI: InChI=1S/C20H30N2O7/c1-13-16(24)17(25)18(26)19(29-13)22-15(23)10-6-3-7-11-21-20(27)28-12-14-8-4-2-5-9-14/h2,4-5,8-9,13,16-19,24-26H,3,6-7,10-12H2,1H3,(H,21,27)(H,22,23)/t13?,16-,17+,18?,19+/m1/s1
• InChIKey: MDHPQXZYOTUIEH-QDGOWHKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-(5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]carbamoyl}pentyl)carbamate
• IUPAC Traditional name: benzyl N-(5-{[(2S,4S,5S)-3,4,5-trihydroxy-6-methyloxan-2-yl]carbamoyl}pentyl)carbamate
• Synonyms: [6-[(6-Deoxy-β-L-galactopyranosyl)amino]-6-oxohexyl]carbamic Acid Phenylmethyl Ester; N-[(ε-Benzyloxycarbonylamino)caproyl]-β-L-fucopyranosylamine

Database IDs

• CAS Number: 35978-96-2
• PubChem SID: 162255830
• PubChem CID: 71313873

CALCULATED PROPERTIES

• Acid pKa: 11.556638
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): 0.4796273
• LogD (pH = 7.4): 0.4796006
• Log P: 0.47962785
• Molar Refractivity: 103.1771 cm^3
• Polarizability: 41.14418 Å^3
• Polar Surface Area: 137.35 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Warm Ethanol; Warm Water
• Apperance: White Crystalline Solid
• Melting Point: 173-175°C

DETAILS

Toronto Research Chemicals - B285890

Used for the isolation of L-fucose binding proteins using affinity chromatography.

REFERENCES

• Biochim. Biophys. Acta, 264(1)
• 171 (1972)