Benzyl-2-acetamido-2-deoxy-α-D-galactopyranoside - ≥98% , CAS No.3554-93-6

CAS: 3554-93-6 Cat. No.: B340877 Molecular Weight: 311.33

GRADE & PURITY ≥98%

Synonyms

A-GalNAc | SCHEMBL542627 | Benzyl- | N-[(2S,3R,4R,5R,6R)-2-(benzyloxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | Benzyl 2-acetamido-2-deoxy-a-D-galactopyranoside | Benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside | Benzyl-alpha-galnac | N-(

Storage

Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Overview

Benzyl-2-acetamido-2-deoxy-α-D-galactopyranoside is used as an inhibitor of O-linked glycosylation in a variety of cell lines. Benzyl-2-acetamido-2-deoxy-a-D-galactopyranoside also inhibits 2,3(O)-sialyltransferase and disrupts glycoprotein targeting in HT-29 cells. Benzyl-2-acetamido-2-deoxy-α-D-galactopyranoside can serve as a substrate for N-acetyl-b-D-glucosaminyltransferase. In Capan-1 and HPAF-II cells, Benzyl-2-acetamido-2-deoxy-α-D-galactopyranoside enhanced cell death induced by 5-fluorouracil.

Specifications

Synonyms

A-GalNAc | SCHEMBL542627 | Benzyl- | N-[(2S, 3R, 4R, 5R, 6R)-2-(benzyloxy)-4, 5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide | Benzyl 2-acetamido-2-deoxy-a-D-galactopyranoside | Benzyl 2-acetamido-2-deoxy-alpha-D-galactopyranoside | Benzyl-alpha-galnac | N-(

Specifications & Purity

≥98%

Storage

Store at -20°C, Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756866
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756866
• Canonical Smiles: CC(=O)NC1C(C(C(OC1OCC2=CC=CC=C2)CO)O)O
• IUPAC Name: N-[(2S,3R,4R,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-phenylmethoxyoxan-3-yl]acetamide
• InChIKey: SKOZFDIGKDPQBO-QMIVOQANSA-N
• INCHI: 1S/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11-,12-,13+,14-,15+/m1/s1
• Isomeric SMILES: CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1OCC2=CC=CC=C2)CO)O)O
• WGK Germany: 3
• Molecular Weight: 311.33
• Reaxy-Rn: 24899645
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=24899645&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic oxygen compounds
    • Class Organooxygen compounds
      • Subclass Carbohydrates and carbohydrate conjugates
        • Level5 Aminosaccharides
          • Level6 N-acyl-alpha-hexosamines

• Kingdom: Organic compounds
• Superclass: Organic oxygen compounds
• Class: Organooxygen compounds
• Subclass: Carbohydrates and carbohydrate conjugates
• Intermediate Tree Nodes: Aminosaccharides
• Direct Parent: N-acyl-alpha-hexosamines
• Alternative Parents: Hexoses O-glycosyl compounds Oxanes Benzene and substituted derivatives Acetamides Secondary carboxylic acid amides Secondary alcohols Oxacyclic compounds Acetals Primary alcohols Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: N-acyl-alpha-hexosamine - Hexose monosaccharide - O-glycosyl compound - Glycosyl compound - Benzenoid - Oxane - Monosaccharide - Monocyclic benzene moiety - Acetamide - Secondary carboxylic acid amide - Secondary alcohol - Carboxamide group - Oxacycle - Organoheterocyclic compound - Carboxylic acid derivative - Acetal - Organic nitrogen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Primary alcohol - Organonitrogen compound - Carbonyl group - Alcohol - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as n-acyl-alpha-hexosamines. These are carbohydrate derivatives containing a hexose moiety in which the oxygen atom is replaced by an n-acyl group.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: Soluble in DMSO, Hot ethanol, water (partly miscible), and methanol.
• Sensitivity: Air,Heat sensitive
• Refractive Index: n20D1.59 (Predicted)
• Boil Point(°C): ~594.9° C at 760 mmHg (Predicted)
• Melt Point(°C): 204-208° C
• Molecular Weight: 311.330 g/mol
• XLogP3: -0.700
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 311.137 Da
• Monoisotopic Mass: 311.137 Da
• Topological Polar Surface Area: 108.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 360.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 5
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1