29776-43-0

Usage

Uses

Used in Carbohydrate Chemistry:
2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-D-GLUCOPYRANOSE is used as a synthetic intermediate for the preparation of pure methyl aand b-glycosides of D-glucosamine. Its application in this field is crucial for the development of new carbohydrate-based compounds and their potential applications in various industries.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-D-GLUCOPYRANOSE can be utilized as a key building block for the synthesis of complex carbohydrate-based drugs. Its ability to form various derivatives makes it a promising candidate for the development of novel therapeutic agents.
Used in Research and Development:
2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-D-GLUCOPYRANOSE is also used in research and development for the study of carbohydrate structures and their interactions with biological systems. This knowledge can lead to a better understanding of various biological processes and the development of targeted therapies for various diseases.
Used in Material Science:
In material science, 2-ACETAMIDO-4,6-O-BENZYLIDENE-2-DEOXY-D-GLUCOPYRANOSE can be employed in the development of novel carbohydrate-based materials with unique properties. These materials could have potential applications in areas such as drug delivery, sensors, and biocompatible materials.

InChI:InChI=1/C15H19NO6/c1-8(17)16-11-12(18)13-10(21-14(11)19)7-20-15(22-13)9-5-3-2-4-6-9/h2-6,10-15,18-19H,7H2,1H3,(H,16,17)/t10-,11-,12-,13-,14?,15?/m1/s1

Upstream product

• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-52-7 benzaldehyde 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 

Downstream Products

• 105453-31-4 2-acetamido-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-β-D-glucopyranose 
• 105453-30-3 2-acetamido-1,3-di-O-acetyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranose 
• 135561-60-3 benzyl <2-acetamido-4,6-O-benzylidene-3-O-<(R)-3-(benzyloxy)tetradecanoyl>-2-deoxy-α-D-glucopyranosyl>acetate 
• 135561-45-4 benzyl <2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-glucopyranosyl>acetate 
• 135561-45-4 benzyl <2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranosyl>acetate 
• 65730-02-1 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 508194-14-7 allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 63064-49-3 allyl 2-acetamido-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 508194-16-9 allyl 2-acetamido-3-O-benzyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 100021-35-0 2-acetamino-2-deoxy-4,6-O-phenylmethylene-1,3-di-O-acetyl-α-D-glucopyranose 
• 1423035-26-0 1,3-di-O-acetyl-4,6-O-benzylidene-2-acetamido-2-deoxy-D-glucopyranoside 
• 1231932-86-7 1,3-di-O-acetyl-6-O-benzyl-2-acetamido-2-deoxy-D-glucopyranoside 
• 124098-05-1 2-methyl-(4,6-O-benzylidene-1,2-dideoxy-α-D-glucopyrano)<2,1-d>-Δ²-oxazoline 
• 105874-58-6 2-Acetamido-4,6-O-benzyliden-2-desoxy-D-glucose-oxim 

Relevant academic research and scientific papers

Novel phosphoramidate prodrugs of N-acetyl-(d)-glucosamine with antidegenerative activity on bovine and human cartilage explants

(d)-Glucosamine and other nutritional supplements have emerged as safe alternative therapies for osteoarthritis (OA), a chronic and degenerative articular joint disease. In our preceding paper, a series of novel O-6 phosphate N-acetyl (d)-glucosamine prod

Synthesis of 1,2-cis- and 1,2-trans-glycosides of 2-acetamido-4,6-O- benzylidene-2-deoxy-d-glucopyranose by anomeric O-alkylation

The reaction of a partially protected 1-hydroxy derivative of N-acetyl-d-glucosamine with benzyl bromide under conditions of anomeric O-alkylation was studied. It was found that the stereoselectivity of the reaction depended on the nature of the alkali me

PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DI- OR OLIGO-SACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF

The present invention relates to a process for the synthesis of L-fucosyl di- or oligosaccharides and their novel 2,3,4-tri-O-benzyl-fucosyl synthetic intermediates derivatives of easy crystallization. In particular the present invention relates to a proc

PROCESS FOR THE SYNTHESIS OF L-FUCOSYL DL- OR OLIGOSACCHARIDES AND NOVEL 2,3,4 TRIBENZYL-FUCOSYL DERIVATIVES INTERMEDIATES THEREOF

The present invention relates to a process for the synthesis of L-fυcosyl di- or oligosaccharides and their novel 2,3,4-tri-O-benzyl-fucosyl synthetic intermediates derivatives of easy crystallization. In particular the present invention relates to a process applicable to industrial scale for the synthesis of 2'O-fucosyl lactose.

Substrate specificity of N-acetylhexosamine kinase towards N-acetylgalactosamine derivatives

We report herein a bacterial N-acetylhexosamine kinase, NahK, with broad substrate specificity towards structurally modified GalNAc analogues, and the production of a GalNAc-1-phosphate library using this kinase.

Synthesis and biological evaluation of a lipid A derivative that contains an aminogluconate moiety

A highly convergent strategy for the synthesis of several derivatives of the lipid A of Rhizobium sin-1 has been developed. The synthetic derivatives are 2-aminogluconate 3 and 2-aminogluconolactone 4, both of which lack C-3 acylation. These derivatives w

Palladium-catalysed asymmetric allylic alkylation using new chiral phosphinite-nitrogen ligands derived from D-glucosamine

Novel phosphinite-nitrogen chiral ligands synthesized from D-glucosamine furnish a high level of enantiomeric excess (up to 96% ee] in palladium-catalysed allylic alkylation.

Palladium-catalyzed asymmetric allylic substitution reactions using new chiral phosphinite-oxazoline ligands derived from D-glucosamine

Novel 2-alkyl- or 2-aryl-4,5-(4,6-O-benzylidene-3-O-(diphenylphosphino)- 1,2-dideoxy-α-D-glucopyrano)-[2,1-d]-2-oxazolines (5a-f) have been prepared from D-glucosamine hydrochloride. They work effectively as chiral ligands and provide a high level of enantiomeric excess in palladium-catalyzed allylic alkylation and amination reactions. The allylic alkylation of 1,3-diphenyl-3- acetoxyprop-1-ene with dimethyl malonate proceeds smoothly in the presence of 0.25 mol % [Pd(η3C3H5)Cl]2 and the chiral ligand 5a having the smallest substituent on oxazoline at 0 °C within 6 h to furnish the highest enantiomeric excess (96% ee). The ligand 5a is also effective for the Pd- catalyzed amination of ethyl 1,3-diphenylprop-2-enyl carbonate, leading to the corresponding allylic amine in 94% ee. The full scope and limitations using ligands 5a-f in the allylic substitution reactions are described.