78247-23-1

Upstream product

• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 100-52-7 benzaldehyde 
• 100-51-6 benzyl alcohol 
• 1009644-15-8 benzyl 2-amino-4,6-O-benzylidene-2-deoxy-α-D-altropyranoside 
• 10380-86-6 phenylmethyl 2-acetylamino-2-deoxy-α-D-mannopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 399032-16-7 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-methanesulfonyl-α-D-glucopyranoside 
• 108-22-5 Isopropenyl acetate 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 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

• 572909-53-6 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-glucopyranoside 
• 74842-55-0 N-acetyl-1-O-benzyl-4,6-O-benzylidenemuramic acid 
• 13347-83-6 benzyl 4,6-O-benzylidene-2-amino-2-deoxy-α-D-glucopyranoside 
• 94902-89-3 benzyl 2-acetamido-3-azido-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside 
• 107983-28-8 benzyl 2-acetamido-3-amino-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside 
• 95451-84-6 benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid 
• 95451-85-7 (Benzyl-2-acetamido-3-O-benzyl-2-desoxy-α-D-mannopyranosid)uronsaeure 
• 95530-21-5 (Benzyl-2-<(benzyloxycarbonyl)amino>-2-desoxy-α-D-mannopyranosid)uronsaeure 
• 42890-09-5 Benzyl-2-<(benzyloxycarbonyl)amino>-2-desoxy-α-D-mannopyranosid 

Relevant academic research and scientific papers

Phosphoramidates of monosaccharides

The present invention relates novel phosphoramidates of monosaccharides of formula (I), wherein R1 is a monosaccharide group selected from A and B; R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14, R15, R16 and X are as defined herein. Preferably X is -O-. The present invention also provides processes for the production of compounds of formula (I), pharmaceutical compositions comprising these compounds, as well as to the use thereof in medical therapy, preferably in the treatment of osteoarthritis. wherein: R1 is selected from A and B,

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 novel carbohydrate-based chiral P, N ligands and their applications in Cu-catalyzed enantioselective 1, 4-conjugate additions

A new type of phosphate-pyridine (P, N) ligand derived from d-glucosamine and BINOL was synthesized and successfully applied in Cu-catalyzed enantioselective conjugate addition of diethylzinc to chalcones for the first time, high yields and enantioselectivities were obtained when the ligand 10a which contains (S)-BINOL was used. The results also showed that the configuration of BINOL at the ligand backbone had remarkable effects on the activities and enantioselectivities.

Chemical synthesis of UDP-Glc-2,3-diNAcA, a key intermediate in cell surface polysaccharide biosynthesis in the human respiratory pathogens B. pertussis and P. aeruginosa

In connection with studies on lipopolysaccharide biosynthesis in respiratory pathogens we had a need to access potential biosynthetic intermediate sugar nucleotides. Herein we report the chemical synthesis of uridine 5′-diphospho 2,3-diacetamido-2,3-dideoxy-α-D-glucuronic acid (UDP-Glc-2,3-diNAcA) (1) from N-acetyl-D-glucosamine in 17 steps and ～9% overall yield. This compound has proved invaluable in the elucidation of biosynthetic pathways leading to the formation of 2,3-diacetamido-2,3-dideoxy-D- mannuronic acid-containing polysaccharides. The Royal Society of Chemistry 2009.

Optimization of UDP-N-acetylmuramic acid synthesis

UDP-N-acetylmuramic acid (UDP-MurNAc) is a substrate of MurC, an important enzyme in the intracellular pathway of bacterial peptidoglycan biosynthesis. Various approaches towards preparation of UDP-Mur/VAc have been published but these synthetic preparations were shown to include many problematic steps. An optimization study with the focus on muramyl phosphate and UMP-morpholidate coupling was performed, resulting in a synthetic procedure enabling robust and easily reproducible production on a multi-gram scale.

Synthesis of anomerically pure, furanose-free α-benzyl-2-amino-2- deoxy-D-altro- and D-manno-pyranosides and some of their derivatives

The anomerically pure benzyl α-d-glycoside of 2-amino-2-deoxy- mannopyranoside was synthesized from d-glucopyranose via 2-amino-2-deoxy-d- altrose intermediates. Unlike the direct synthesis from mannosamine in the literature, our method provides furanose-

Fluorinated glucosamine analogs useful for modulating post-translational glycosylations on cells

The present invention provides compositions and methods for inhibiting cell migration, e.g., lymphocytes and inflammation. The invention also provides an improved process for preparing fluorinated N-acetylglucosamines.

Metal-catalyzed acyl transfer reactions of enol esters: Role of Y5(OiPr)13O and (thd)2Y(OiPr) as transesterification catalysts

(equation presented) Primary and secondary alcohols react with vinyl or isopropenyl acetate at room temperature in the presence of catalytic amounts (0.05-1 mol percent) of Y5(OiPr)13O to give the corresponding esters. In selected cases, the yttrium catalyst promotes the selective O-acylation of amino alcohols without the formation of the amide. Enol esters also react with α-amino acid esters in the absence of a catalyst, at room temperature, to give the corresponding amides.

ERPROBTE SYNTHESE VON 2-AZIDO-2-DESOXY-D-MANNOSE UND 2-AZIDO-2-DESOXY-D-MANNURONSAEURE ALS BAUSTEIN ZUM AUFBAU VON BAKTERIEN-POLYSACCHARID-SEQUENZEN

The azidonitration of 3,4,6-tri-O-acetyl-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol at low temperature afforded preponderantly the azidonitrate having the D-manno configuration.After reaction with sodium acetate, 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-α-D-mannopyranose was directly isolated and deblocking gave 2-azido-2-deoxy-D-mannopyranose. 3,4,6-Tri-O-acetyl-2-azido-2-deoxy-α-D-mannopyranosyl bromide and 2-azido-3,4,6-tri-O-benzyl-α-D-mannopyranosyl bromide were prepared and are suitable for selective α- and β-glycoside synthesis.In the presence of platinum-oxygen, the catalytic oxidation of benzyl 2-azido-2-deoxy-α-D-mannopyranoside gave in high yields (benzyl 2-azido-2-deoxy-α-D-mannopyranosid)uronic acid from which 2-amino-2-deoxy-D-mannopyranuronic acid was obtained.By catalytic oxidation, selectively blocked derivatives of 2-amino-2-deoxy-D-mannopyranose were converted into the correspondind uronic acid derivatives.