53167-38-7

Basic information

• Product Name: BENZYL 2-ACETAMIDO-2-DEOXY-4-O-(BETA-D-GALACTOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE
• Synonyms: Benzyl 2-Acetamido-2-deoxy-4-O-(-D-galactopyranosyl)--D-glucopyranoside;Gal1--4GlcNAc--Bn;PhenylMethyl 2-(AcetylaMino)-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside;Benzyl 2-Acetamido-2-deoxy-4-O-(β-D-galactopyranosyl)-β-\nD-glucopyranoside
• CAS NO: 53167-38-7
• Molecular Formula: C₂₁H₃₁NO₁₁
• Molecular Weight: 473.472
• Product Categories: Oligosaccharides
• Mol File: 53167-38-7.mol
• Article Data: 3

Chemical Properties

• Melting Point: 241-244°C
• Boiling Point: 802.921°C at 760 mmHg
• Flash Point: 439.391°C
• Appearance: /
• Density: 1.496g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.624
• Storage Temp.: -20°C Freezer
• Solubility: Methanol, Water
• CAS DataBase Reference: BENZYL 2-ACETAMIDO-2-DEOXY-4-O-(BETA-D-GALACTOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: BENZYL 2-ACETAMIDO-2-DEOXY-4-O-(BETA-D-GALACTOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE(53167-38-7)
• EPA Substance Registry System: BENZYL 2-ACETAMIDO-2-DEOXY-4-O-(BETA-D-GALACTOPYRANOSYL)-BETA-D-GLUCOPYRANOSIDE(53167-38-7)

Safety Data

• Hazardous Substances Data: 53167-38-7(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

InChI:InChI=1/C21H31NO11/c1-10(25)22-14-16(27)19(33-21-18(29)17(28)15(26)12(7-23)31-21)13(8-24)32-20(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-/m0/s1

Upstream product

• 81243-74-5 benzyl 3,6-di-O-acetyl-2-deoxy-2-phthalimido-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 87190-71-4 O-<(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->4)-3,6-di-O-acetyl-2-desoxy-2-phthalimido-β-D-glucopyranosyl>trichloracetimidat 
• 100-51-6 benzyl alcohol 
• 175436-17-6 UDP-Gal 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 53167-37-6 benzyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranoside 
• 53167-36-5 2-methyl{3,6-di-O-acetyl-1,2-dideoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyrano}[2,1-d]oxazoline 
• 36954-63-9 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-2-deoxy-2-acetamido-1,3,4-tri-O-acetyl-α-D-glucopyranose 

Downstream Products

• 86427-89-6 N-[(2R,3R,4R,5R,6R)-2-Benzyloxy-4-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-trimethylsilanyloxy-6-trimethylsilanyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 212198-11-3 2,2-Dimethyl-propionic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-3-[(2S,3R,4S,5S,6R)-4-(2,2-dimethyl-propionyloxy)-6-(2,2-dimethyl-propionyloxymethyl)-3,5-dihydroxy-tetrahydro-pyran-2-yloxy]-4-hydroxy-tetrahydro-pyran-2-ylmethyl ester 
• 212198-13-5 2,2-Dimethyl-propionic acid (2S,3R,4S,5S,6R)-3,5-diacetoxy-2-[(2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-(2,2-dimethyl-propionyloxymethyl)-4-hydroxy-tetrahydro-pyran-3-yloxy]-6-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-pyran-4-yl ester 
• 212198-12-4 C₃₉H₅₆Cl₃NO₁₆ 
• 212198-25-9 C₄₃H₆₀Cl₃NO₁₈ 

Relevant articles and documents

Specificity of β1,4-galactosyltransferase inhibition by 2-naphthyl 2-butanamido-2-deoxy-1-thio-β-D-glucopyranoside

Inhibitors of Galactosyltransferase (GalT) have the potential of reducing the amounts of adhesive carbohydrates on secreted and cell surface-bound glycoproteins. We recently found a potent inhibitor of β4GalT, 2-naphthyl 2-butanamido-2-deoxy-1-thio-β-D-glucopyranoside (compound 612). In this work, we have tested compound 612 for the specificity of its inhibition and examined its effect on GalT, and on GlcNAc- and GalNAc-transferases in homogenates of different cell lines, as well as on recombinant glycosyltransferases. Compound 612 was found to be a specific inhibitor of β4GalT. The specificity of recombinant human β3GalT5 that also acts on GlcNAc-R substrates, revealed similarities to bovine milk β4GalT. However, 612 was a poor substrate and not an inhibitor for β3GalT5. To further determine the specific structures responsible for the inhibitory property of 612, we synthesized (2-naphthyl)-2-butanamido-2-deoxy-β-D- glucopyranosylamine (compound 629) containing nitrogen in the glycosidic linkage, and compared it to other naphthyl and quinolinyl derivatives of GlcNAc as substrates and inhibitors. Compound 629 was a substrate for both β4GalT and β3GalT5. This suggests that properties of 612 other than the presence of the naphthyl ring alone were responsible for its inhibitory action. The results suggest a usefulness of 612 in specifically blocking the synthesis of type 2 chains and thus epitopes attached to type 2 chains. In addition, 612 potently inhibits β4GalT in cell homogenates and thus allows assaying β3GalT activity in the presence of β4GalT.

Novel synthetic approaches to manβ1-4GLCNAc and LeX units from N-acetyllactosamine

Regioselective protection of N-acetyllactosamine with triphenylmethyl (trityl) and pivaloyl groups afforded the corresponding 3, 2′, 4′-tri- and 2′,4′-dihydroxyl derivatives in a few steps, respectively; these derivatives were used efficiently for the syntheses of the title compounds from N-acetyllactosamine in 46% (7 steps) and 19% (8 steps) overall yields, respectively.