10380-86-6

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-51-6 benzyl alcohol 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 74034-09-6 2-acetamido-1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-glucitol 
• 100-39-0 benzyl bromide 
• 35812-81-8 Benzyl-2-amino-2-desoxy-α-D-mannopyranosid 
• 108-24-7 acetic anhydride 
• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10294-12-9 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-α,β-D-mannopyranose 
• 4539-83-7 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-mannopyranose 
• 2873-29-2 D-glucal triacetate 
• 95451-80-2 Benzyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-mannopyranosid 
• 68733-20-0 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranoside 
• 95451-81-3 Benzyl-2-azido-2-desoxy-α-D-mannoopyranosid 

Downstream Products

• 13343-61-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 50605-12-4 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 122351-25-1 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-(diphenyl phosphate) 
• 87735-36-2 benzyl 2-acetamido-6-bromo-2,6-dideoxy-β-D-glucopyranoside 
• 206751-91-9 benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 139893-41-7 N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 851189-13-4 benzyl 2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 
• 250734-79-3 Acetic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-81-7 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-61-3 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-83-9 Acetic acid (2S,3R,4S,5R,6R)-2-[(2R,3R,4R,6R)-3-acetylamino-2-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-oxo-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-77-1 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,4aR,6R,7R,8R,8aS)-7-acetylamino-6-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 14855-31-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 50605-13-5 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 

Relevant academic research and scientific papers

Facile approach to 2-acetamido-2-deoxy-β-D-glucopyranosides via a furanosyl oxazoline

(Chemical Equation Presented) A concise and convenient route that may be easily scaled is reported for the preparation of unprotected β-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding β-D-glucopyranosides in good to high yields. Primary alcohols gave only β-D-glucopyranosides. A mechanism is proposed for this transformation.

Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments

Peptidoglycan (PG) is the core structural motif of the bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically relevant amino acid modifications and peptide cross-linkages, is presented using solution and solid phase approaches.

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).

Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives

6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts

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

Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis

Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-

Sugar derived alkamine catalytic imine reduction method

The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.

Chemo-enzymatic approach to access diastereopure α-substituted GlcNAc derivatives

The formation of diastereopure α-substituted GlcNAc derivatives in a simple and straightforward way is a challenging task. Herein, we report the chemical synthesis of diastereomeric α/β-substituted GlcNAc derivatives under non-anhydrous atmosphere using u