6205-72-7

Usage

InChI:InChI=1/C10H18N2O6/c1-4(14)11-7-9(17)8(16)6(3-13)18-10(7)12-5(2)15/h6-10,13,16-17H,3H2,1-2H3,(H,11,14)(H,12,15)/t6-,7-,8-,9-,10-/m1/s1

Upstream product

• 4229-38-3 2-acetamido-2-deoxy-β-D-glucopyranosylamine 
• 108-24-7 acetic anhydride 
• 29847-23-2 2-N-acetylamido-2-deoxy-β-D-glucopyranosyl azide 
• 507-09-5 tiolacetic acid 
• 127-17-3 2-oxo-propionic acid 
• 103955-15-3 2-acetamido-2-deoxy-D-glucose oxime 
• 4515-24-6 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosylamine 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 71142-00-2 2-acetamido-1-N-acetyl-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosylamine 

Downstream Products

• 3530-15-2 3,5-dimethyl-4H-1,2,4-triazol-4-amine 
• 18615-50-4 1-N-acetyl-2-amino-2-deoxy-β-D-glucopyranosylamine 
• 1068-57-1 acetic acid hydrazide 
• 77045-60-4 2-amino-2-deoxy-D-glucose hydrazone 

Relevant academic research and scientific papers

RuCl3-promoted amide formation from azides and thioacids

Described here is the Ru(III)-promoted amide formation from azides and thioacids, which were shown not to form amides at room temperature in the absence of ruthenium. We belive that a complex formed by Ru(III) increases the reactivity of thiocarbonyl species and therefore reaction with azides occurs at room temperature, even when less reactive (electron rich and/or sterically hindered) azides are employed.

Radical-Mediated Acyl Thiol-Ene Reaction for Rapid Synthesis of Biomolecular Thioester Derivatives

The thiol-ene ‘click’ reaction has emerged as a versatile process for carbon–sulfur bond formation with widespread applications in chemical biology, medicinal chemistry and materials science. Thioesters are key intermediates in a wide range of synthetic and biological processes and efficient methods for their synthesis are of considerable interest. Herein, we report the first examples of acyl-thiol-ene (ATE) for the synthesis of biomolecular thioesters, including peptide, lipid and carbohydrate derivatives. A key finding is the profound effect of the amino acid side chain on the outcome of the ATE reaction. Furthermore, radical generated thioesters underwent efficient S-to-N acyl transfer and desulfurisation to furnish ‘sulfur-free’ ligation products in an overall amidation process with diverse applications for chemical ligation and bioconjugation.

Chemoselective coupling of sugar oximes and α-ketoacids to glycosyl amides and N-glycopeptides

The reaction of unprotected sugar hydroxylamines and oximes with α-ketoacids leads to the chemoselective formation of glycosyl amides following the decarboxylative condensation pathway of Bode's ketoacid hydroxylamine (KAHA) ligation. Sugar oximes with gl

Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-beta-D-glycopyranosylamine derivatives and related analogs.

Several 1-N-substituted derivative [haloacetyl-, glycyl-, (dimethyl)amino-acetyl-, azidoacetyl-, trifluoroacetyl-, and trifluoromethylsulfonyl-] of 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-beta-D-glucopyranosylamine (1) were synthesized as potential metabolic inhibitors of cellular-membrane glycoconjugates. Several fully acetylated derivatives were found to inhibit growth of mouse mammary adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction.