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

• ChemBase ID: 76095
• Molecular Formular: C21H31NO11
• Molecular Mass: 473.47094
• Monoisotopic Mass: 473.18971082
• SMILES: CC(=O)N[C@H]1[C@@H](OCc2ccccc2)O[C@H](CO)[C@H](O)[C@@H]1O[C@@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O
• Canonical SMILES: OC[C@H]1O[C@H](OCc2ccccc2)[C@@H]([C@H]([C@H]1O)O[C@@H]1O[C@H](CO)[C@@H]([C@@H]([C@H]1O)O)O)NC(=O)C
• InChI: InChI=1S/C21H31NO11/c1-10(25)22-14-19(33-21-18(29)17(28)15(26)12(7-23)32-21)16(27)13(8-24)31-20(14)30-9-11-5-3-2-4-6-11/h2-6,12-21,23-24,26-29H,7-9H2,1H3,(H,22,25)/t12-,13-,14-,15+,16+,17+,18-,19-,20+,21+/m1/s1
• InChIKey: MYDRTQFLXCNCAG-YOADDMFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)-4-{[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-3-yl]acetamide
• IUPAC Traditional name: β-D-Gal-(1->3)-α-D-GalNAc-OBn
• Synonyms: Phenylmethyl 2-(Acetylamino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside; Gal1-β-3GalNAc-α-O-Bn; Benzyl 2-Acetamido-2-deoxy-3-O-(β-D-galactopyranosyl) α-D-galactopyranoside; Benzyl-2-acetamido-2-deoxy-3-O-beta-D-galactopyranosyl-alpha-D-galactopyranoside

Database IDs

• CAS Number: 3554-96-9
• MDL Number: MFCD00057916
• PubChem SID: 162041011
• PubChem CID: 5288344

CALCULATED PROPERTIES

• Acid pKa: 11.937178
• H Acceptors: 11
• H Donor: 7
• LogD (pH = 5.5): -2.6238108
• LogD (pH = 7.4): -2.6238225
• Log P: -2.6238105
• Molar Refractivity: 108.8018 cm^3
• Polarizability: 44.48356 Å^3
• Polar Surface Area: 187.4 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White to Off-White Solid
• Melting Point: 218-220°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Apollo Scientific Ltd - OR1253T

A substrate for UDP-GlcNAc:Gal1-b-3GalNAc(GlcNAc-GalNAc)-6-b-GlcNAc transferase & sialytransferase.

Toronto Research Chemicals - B212530

Useful as a substrate for UDP-GlcNAc:Gal1-beta-3GalNAc(GlcNAc-GalNAc)-6-beta-GlcNAc transferase and sialytransferase.

REFERENCES

• Li, M., et al.: Biochem., 47, 11590 (2002)
• Hoh, C., et al.: Bioorg. Med. Chem. Lett., 12, 1031 (2002)