10375-65-2

Upstream product

• 100-51-6 benzyl alcohol 
• 51533-00-7 2-acetylamino-3,4,6-triacetyl-2-deoxy-α-D-glucopyranosyl bromide 
• 134160-64-8 4',5'-epoxypentyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 108-24-7 acetic anhydride 
• 22314-39-2 (2R,3S,4R,5R,6R)-5-Amino-6-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 3006-60-8 1,3,4,6-tetra-O-acetyl-2-acetamido-2-deoxy-α,β-D-mannopyranose 
• 72-87-7 N-acetyl-D-mannosamine 
• 22314-39-2 phenylmethyl 2-amino-2-deoxy-α-D-glucopyranoside 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 126777-99-9 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-β-D-glucoopyranosyl azide 
• 126777-92-2 3,4,6-tetra-O-acetyl-2-deoxy-2-iodo-α-D-mannopyranosyl azide 

Downstream Products

• 109068-32-8 benzyl-(2-acetylamino-tri-O-methyl-2-deoxy-β-D-glucopyranoside) 
• 3055-51-4 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 
• 13343-61-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 benzyl 3,4,6-tri-O-acetyl-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 50605-12-4 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 50605-13-5 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 14855-31-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant academic research and scientific papers

New procedure for the preparation of 2-(trimethylsilyl)ethyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside and other alkyl β-glycosides

The title compound and other alkyl β-glycosides 1a-g can be prepared in one step from commercially available 2-acetamido-2-deoxy-1,3,4,6-tetra-O-acetyl-β-D-glucopyranose (3) and simple alcohols using camphorsulfonic acid as a promoter together with azeotr

A practical method for preparation of β-glycosides of N-acetylglucosamine

A mild and efficient method for preparation of GlcNAc derivatives by reaction of glycosyl acceptors with glycosyl oxazolines has been developed. The key feature is use of Yb(OTf)3 as promoter, requiring moderate reaction times and equivalence s

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

Synthesis of N-acetylsugar-β-trans-glycosides: Facile one-pot transglycosylation of epoxypentyl tri-0-acetyl-N-acetylglucosamine

Glycosides 10 and 11 were prepared from epoxypentyl β-D-N-acetylglucosamine 8 under mild conditions, using TMS triflate as the promotor. Presumably, this novel reaction proceeds via in situ activation of the intermediate oxazoline 9.

N-Acetylglucosamine-based efficient, phase-selective organogelators for oil spill remediation

Two simple, eco-friendly and efficient phase-selective gelators were developed for instant (45 s) gelation of oil (either commercial fuels or pure organic liquids) from an oil-water mixture at room temperature to combat marine oil spills.

H2so4-silica promoted direct formation of β-glycosides of N-Acetyl glycosylamines under microwave conditions

N-Acetyl glycosamines are important building blocks for the synthesis of biologically active oligosaccharides. This communication describes a simple direct protocol for the synthesis of βglycosides of N-acetyl glycosylamines from easily accessible perO-ac

The effect of deoxyfluorination and: O -acylation on the cytotoxicity of N -acetyl-d-gluco- And d-galactosamine hemiacetals

Fully acetylated deoxyfluorinated hexosamine analogues and non-fluorinated 3,4,6-tri-O-acylated N-acetyl-hexosamine hemiacetals have previously been shown to display moderate anti-proliferative activity. We prepared a set of deoxyfluorinated GlcNAc and GalNAc hemiacetals that comprised both features: O-acylation at the non-anomeric positions with an acetyl, propionyl and butanoyl group, and deoxyfluorination at selected positions. Determination of the in vitro cytotoxicity towards the MDA-MB-231 breast cancer and HEK-293 cell lines showed that deoxyfluorination enhanced cytotoxicity in most analogues. Increasing the ester alkyl chain length had a variable effect on the cytotoxicity of fluoro analogues, which contrasted with non-fluorinated hemiacetals where butanoyl derivatives had always higher cytotoxicity than acetates. Reaction with 2-phenylethanethiol indicated that the recently described S-glyco-modification is an unlikely cause of cytotoxicity.

Targeting GNE Myopathy: A Dual Prodrug Approach for the Delivery of N-Acetylmannosamine 6-Phosphate

ProTides comprise an important class of prodrugs currently marketed and developed as antiviral and anticancer therapies. The ProTide technology employs phosphate masking groups capable of providing more favorable druglike properties and an intracellular activation mechanism for enzyme-mediated release of a nucleoside monophosphate. Herein, we describe the application of phosphoramidate chemistry to 1,3,4-O-acetylated N-acetylmannosamine (Ac3ManNAc) to deliver ManNAc-6-phosphate (ManNAc-6-P), a critical intermediate in sialic acid biosynthesis. Sialic acid deficiency is a hallmark of GNE myopathy, a rare congenital disorder of glycosylation (CDG) caused by mutations in GNE that limit the production of ManNAc-6-P. Synthetic methods were developed to provide a library of Ac3ManNAc-6-phosphoramidates that were evaluated in a series of studies for their potential as a treatment for GNE myopathy. Prodrug 12b showed rapid activation in a carboxylesterase (CPY) enzymatic assay and favorable ADME properties, while also being more effective than ManNAc at increasing sialic acid levels in GNE-deficient cell lines. These results provide a potential platform to address substrate deficiencies in GNE myopathy and other CDGs.

MONOSACCHARIDE PHOSPHORAMIDATE PRODRUGS

The present disclosure provides monosaccharide phosphoramidate prodrugs of monosaccharide monophosphates. The present disclosure further provides methods of treating diseases of conditions such as congenital disorders of glycosylation comprising administering the monosaccharide phosphoramidate prodrugs of the present disclosure to a patient in need thereof.

Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases

The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).