N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-5-hydroxy-6-methyl-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide

• ChemBase ID: 161345
• Molecular Formular: C21H31NO10
• Molecular Mass: 457.47154
• Monoisotopic Mass: 457.1947962
• SMILES: [C@H]1([C@@H]([C@@H]([C@@H](O[C@H]1CO)O[C@@H]1[C@@H]([C@H](O[C@H]([C@@H]1O)C)OCc1ccccc1)NC(=O)C)O)O)O
• Canonical SMILES: OC[C@@H]1O[C@@H](O[C@@H]2[C@H](NC(=O)C)[C@@H](OCc3ccccc3)O[C@H]([C@@H]2O)C)[C@H]([C@H]([C@H]1O)O)O
• InChI: InChI=1S/C21H31NO10/c1-10-15(25)19(32-21-18(28)17(27)16(26)13(8-23)31-21)14(22-11(2)24)20(30-10)29-9-12-6-4-3-5-7-12/h3-7,10,13-21,23,25-28H,8-9H2,1-2H3,(H,22,24)/t10-,13-,14-,15+,16+,17+,18-,19-,20+,21+/m1/s1
• InChIKey: HGURJGMYXKMOOM-QAYXKSKNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-5-hydroxy-6-methyl-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: N-[(2S,3R,4R,5S,6R)-2-(benzyloxy)-5-hydroxy-6-methyl-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• Synonyms: Phenylmethyl 2-(Acetylamino)-2,6-dideoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside; Galβ1-3GalNAcα-Bn; Benzyl 2-Acetamido-2,6-dideoxy-3-O-β-D-galactopyranosyl α-D-Galactopyranoside

Database IDs

• CAS Number: 141020-28-2
• PubChem SID: 162255480
• PubChem CID: 71313741

CALCULATED PROPERTIES

• Acid pKa: 11.966909
• H Acceptors: 10
• H Donor: 6
• LogD (pH = 5.5): -1.5769008
• LogD (pH = 7.4): -1.5769118
• Log P: -1.5769005
• Molar Refractivity: 107.2581 cm^3
• Polarizability: 43.79805 Å^3
• Polar Surface Area: 167.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B211740

Benzyl 2-Acetamido-2,6-dideoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside is useful in the biosynthesis of O-glycoproteins.

REFERENCES

• Kuhns, W., et al.: Glycoconjugate J., 10, 381 (1993)
• Orlacchio, A., et al.: J. Neurological Sci., 151, 177 (1993)