23661-33-8

Basic information

• Product Name: methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside
• Synonyms: methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside
• CAS NO: 23661-33-8
• Molecular Weight: 474.486
• Mol File: 23661-33-8.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside(23661-33-8)
• EPA Substance Registry System: methyl 2,3,4-tri-O-acetyl-6-O-(p-tolylsulfonyl)-α-D-glucopyranoside(23661-33-8)

Safety Data

• Hazardous Substances Data: 23661-33-8(Hazardous Substances Data)

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 7432-72-6 methyl 2,3,4-tri-O-acetyl-α-D-glucopyranose 
• 108-24-7 acetic anhydride 
• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 

Downstream Products

• 6619-09-6 methyl 6-O-tosyl-α-D-glucopyranoside 
• 23701-87-3 methyl 6-azido-6-deoxy-α-D-glucopyranoside 
• 5155-47-5 methyl 6-amino-6-deoxy-α-D-glucopyranoside 
• 17184-28-0 Methyl-3,6-anhydro-α-D-glucofuranosid 
• 59202-80-1 Acetic acid (2R,3R,4S,5R)-4,5-diacetoxy-6-bromo-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 69240-09-1 2,3,4-tri-O-acetyl-1,5-anhydro-6-O-(4-methylphenylsulfonyl)-D-arabino-hex-1-enitol 
• 871011-08-4 2,3,4-tri-O-acetyl-1-S-methylsulfonyl-6-O-(4-methylphenylsulfonyl)-1-thio-β-D-glucose 
• 871010-58-1 2,3,4-tri-O-acetyl-6-S-acetyl-S-phenylsulfonyl-1,6-dithio-β-D-glucose 
• 20113-43-3 1,2,3,4-tetra-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranose 
• 21893-05-0 methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside 

Relevant articles and documents

Synthesis and Evaluation of the Biological Profile of Novel Analogues of Nucleosides and of Potential Mimetics of Sugar Phosphates and Nucleotides

The synthesis of purine/triazole 6'-isonucleosides and of glucuronic acid/glucuronamide-derived N-glycosylsulfonohydrazides through efficient and stereo- or regioselective methodologies is described. Their structures were envisaged to mimic nucleosides, s

Phosphatidylinositol 3-phosphate mimics based on a sulfoquinovose scaffold: Synthesis and evaluation as protein kinase B inhibitors

New sulfoquinovose analogues of phosphatidylinositol 3-phosphate have been synthesised based on a sulfoquinovose scaffold as potential protein kinase B (PKB) inhibitors. The synthetic strategy involved the introduction into glucose of a thioacetate group at the 6-position and of an azide group at the anomeric position as precursors of the sulfonate and phosphoramidate moieties present in the final compounds. The synthesised compounds were tested in vitro on isolated PKB by means of ELISA assays and for their anti-proliferative activity against the human ovarian carcinoma cell line IGROV-1. Sulfoquinovose derivatives 2b and 2c showed inhibitory activity in the low micromolar range.

Development and characterization of lysine based tripeptide analogues as inhibitors of Sir2 activity

Sirtuins are NAD+ dependent deacetylases that modulate various essential cellular functions. Development of peptide based inhibitors of Sir2s would prove useful both as pharmaceutical agents and as effectors by which downstream cellular alterations can be monitored. Click chemistry that utilizes Huisgen's 1,3-dipolar cycloaddition permits attachment of novel modifications onto the side chain of lysine. Herein, we report the synthesis of peptide analogues prepared using click reactions on Nε-propargyloxycarbonyl protected lysine residues and their characterization as inhibitors of Plasmodium falciparum Sir2 activity. The peptide based inhibitors exhibited parabolic competitive inhibition with respect to acetylated-peptide substrate and parabolic non-competitive inhibition with NAD+ supporting the formation of EI2 and E·NAD+·I2 complexes. Cross-competition inhibition analysis with the non-competitive inhibitor nicotinamide (NAM) ruled out the possibility of the NAM-binding site being the second inhibitor binding site, suggesting the presence of a unique alternate pocket accommodating the inhibitor. One of these compounds was also found to be a potent inhibitor of the intraerythrocytic growth of P. falciparum with 50% inhibitory concentration in the micromolar range.