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

• ChemBase ID: 161696
• Molecular Formular: C20H30N2O8
• Molecular Mass: 426.4608
• Monoisotopic Mass: 426.20021593
• SMILES: N(C(=O)CCCCCNC(=O)OCc1ccccc1)[C@H]1C([C@H]([C@H](C(O1)CO)O)O)O
• Canonical SMILES: OCC1O[C@@H](NC(=O)CCCCCNC(=O)OCc2ccccc2)C([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C20H30N2O8/c23-11-14-16(25)17(26)18(27)19(30-14)22-15(24)9-5-2-6-10-21-20(28)29-12-13-7-3-1-4-8-13/h1,3-4,7-8,14,16-19,23,25-27H,2,5-6,9-12H2,(H,21,28)(H,22,24)/t14?,16-,17-,18?,19+/m0/s1
• InChIKey: YRKGECJVSSEXFG-FLYLVDQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: benzyl N-(5-{[(2R,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}pentyl)carbamate
• IUPAC Traditional name: benzyl N-(5-{[(2R,4S,5R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]carbamoyl}pentyl)carbamate
• Synonyms: [6-(β-D-Galactopyranosylamino)-6-oxohexyl]carbamic Acid Phenylmethyl Ester; N-N-Benzyloxycarbonyl-ε-aminocaproyl-β-D-galactopyranosylamine; N-(ε-N-Benzyloxycarbonylamino)caproyl)-β-D-galactopyranosylamine (contains approx 35% Ethanol)

Database IDs

• CAS Number: 38822-58-1
• PubChem SID: 162255831
• PubChem CID: 71313874

CALCULATED PROPERTIES

• Acid pKa: 11.479595
• H Acceptors: 7
• H Donor: 6
• LogD (pH = 5.5): -0.56728274
• LogD (pH = 7.4): -0.5673146
• Log P: -0.56728214
• Molar Refractivity: 104.7208 cm^3
• Polarizability: 41.81435 Å^3
• Polar Surface Area: 157.58 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Warm Ethanol; Warm Water
• Apperance: Off-White Crystalline Solid
• Melting Point: 130-133°C

DETAILS

Toronto Research Chemicals - B285895

Used for the preparation of sugar specific antibodies using liposomes.

REFERENCES

• Indian J. Biochem. Biophys., 22(4)
• 244 (4)
• Chem. Pharm. Bull., 30(4)
• 1753 (1982)