10380-86-6

Basic information

• Product Name: phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside
• Synonyms: phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside
• CAS NO: 10380-86-6
• Molecular Weight: 311.335
• Mol File: 10380-86-6.mol
• Article Data: 43

Chemical Properties

• CAS DataBase Reference: phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside(10380-86-6)
• EPA Substance Registry System: phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside(10380-86-6)

Safety Data

• Hazardous Substances Data: 10380-86-6(Hazardous Substances Data)

Upstream product

• 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 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 10375-65-2 Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yl ester 
• 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 
• 95451-93-7 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide 

Downstream Products

• 13320-00-8 benzyl 2-acetamido-3-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 189683-17-8 Acetic acid (2S,3S,4R,5R,6S)-4,5-diacetoxy-2-((2R,3S,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-ylsulfanyl)-6-methyl-tetrahydro-pyran-3-yl ester 
• 19374-64-2 N-((4aR,6R,7R,8S,8aS)-6-Benzyloxy-8-hydroxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 14040-20-1 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 62867-63-4 benzyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-glucopyranoside 
• 62867-64-5 benzyl 2-acetamido-4-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 134308-75-1 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1287768-23-3 benzyl 2-acetamido-3,6-di-O-benzyl-4-O-propargyl-2-deoxy-β-D-glucopyranoside 
• 1287768-32-4 benzyl 2-acetamido-3-O-propargyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 1287768-33-5 benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 1287768-34-6 benzyl 2-acetamido-3-O-propargyl-6-O-benzyl-2-deoxy-β-D-galactopyranoside 
• 1287768-35-7 benzyl 2-acetamido-3-O-propargyloxy-4-O-acetyl-6-O-benzyl-2-deoxy-β-D-glucopyranoside 

Relevant articles and documents

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.

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 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).