113757-75-8

Upstream product

• 6813-81-6 N-acetyl neuraminic acid 
• 100-39-0 benzyl bromide 
• 501-53-1 benzyl chloroformate 
• 19342-33-7 N-acetyl neuraminic acid 
• 908094-04-2 phenyldiazomethane 
• 99396-00-6 5-acetamido-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosylonic acid 

Downstream Products

• 114857-73-7 benzyl 5-acetamido-3,5-dideoxy-8,9-O-isopropylidene-D-glycero-β-D-galacto-2-nonulopyranosonate 
• 1432039-76-3 C₃₁H₄₀N₂O₁₂ 
• 118190-51-5 5-acetamido-2,4,7,8,9-penta-O-monochloroacetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulosonic acid benzyl ester 
• 115400-37-8 5-acetamido-2-O-benzyl-3,5-dideoxy-D-glycero-D-galacto-2-noneno-1,4-lactone 
• 113757-76-9 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1421960-13-5 C₁₈H₂₄N₂O₇ 
• 1421960-11-3 C₁₉H₂₄N₂O₉ 
• 1421960-28-2 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tertbutoxycarbonyl)guanidino)-6-(3-chlorobenzylcarbamoyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1421960-27-1 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tertbutoxycarbonyl)guanidino)-6-(4-fluorobenzylcarbamoyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1421960-26-0 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tertbutoxycarbonyl)guanidino)-6-(4-methylbenzylcarbamoyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1421960-25-9 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tertbutoxycarbonyl)guanidino)-6-(2-fluorobenzylcarbamoyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1421960-24-8 (1S,2R)-1-((2R,3R,4S)-3-acetamido-4-(2,3-bis(tertbutoxycarbonyl)guanidino)-6-(3-fluorobenzylcarbamoyl)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 1384751-64-7 (1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(2,3-bis(tert-butoxycarbonyl)guanidino)-3,4-dihydro-2H-pyran-2-yl)-propane-1,2,3-triyl triacetate 
• 1421960-02-2 (1S,2R)-1-((2R,3R,4S)-3-acetamido-6-(benzyloxycarbonyl)-4-(tertbutoxycarbonylamino)-3,4-dihydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 

Relevant academic research and scientific papers

Synthesis of partially O-acetylated N-acetylneuraminic acid using regioselective silyl exchange technology

Postglycosylation acetylation of sialic acid imparts unique roles to sialoglycoconjugates in mammalian immune response making structural and functional understanding of these analogues important. Five partially O-acetylated Neu5Ac analogues have been synt

Effective one-pot multienzyme (OPME) synthesis of monotreme milk oligosaccharides and other sialosides containing 4-: O -acetyl sialic acid

A facile one-pot two-enzyme chemoenzymatic approach has been established for the gram (Neu4,5Ac2α3Lac, 1.33 g) and preparative scale (Neu4,5Ac2α3LNnT) synthesis of monotreme milk oligosaccharides. Other O-acetyl-5-N-acetylneuraminic

Structure-based design and synthesis of C-1- and C-4-modified analogs of zanamivir as neuraminidase inhibitors

In order to exploit the 430-cavity in the active sites of neuraminidases, 22 zanamivir analogs with C-1 and C-4 modification were synthesized, and their inhibitory activities against both group-1 (H5N1, H1N1) and group-2 neuraminidases (H3N2) were determined. Compound 9f exerts the most potency, with IC50 value of 0.013, 0.001, and 0.09 μM against H3N2, H5N1, and H1N1, which is similar to that of zanamivir (H3N2 IC50 = 0.0014 μM, H5N1 IC50 = 0.012 μM, H1N1 IC50 = 0.001 μM). Pharmacokinetic studies of compound 9f in rats showed a much longer plasma half-life (t1/2) than that of zanamivir following administration (po dose). Molecular modeling provided information about the binding model between the new inhibitors and neuraminidase, with the elongated groups at the C-1-position being projected toward the 430-loop region. This study may represent a novel starting point for the future development of improved antiflu agents.

SIALIC ACID ANALOGS

The present invention provides sialic acid analogs and their compositions useful for the treatment of sialic acid deficiencies.

Chemoselective synthesis of sialic acid 1,7-lactones

The chemoselective synthesis of the 1,7-lactones of N-acetylneuraminic acid, N-glycolylneuraminic acid, and 3-deoxy-d-glycero-d-galacto-nononic acid is accomplished in two steps: a simple treatment of the corresponding free sialic acid with benzyloxycarbonyl chloride and a successive hydrogenolysis of the formed 2-benzyloxycarbonyl 1,7-lactone. The instability of the 1,7-lactones to protic solvents has been also evidenced together with the rationalization of the mechanism of their formation under acylation conditions. The results permit to dispose of authentic 1,7-sialolactones to be used as reference standards and of a procedure useful for the preparation of their isotopologues to be used as inner standards in improved analytical procedures for the gas liquid chromatography-mass spectrometry (GLC-MS) analysis of 1,7-sialolactones in biological media.

SYNTHESIS OF 9-O-ACYL- AND 4-O-ACETYL-SIALIC ACIDS

Various 9-O-acyl derivatives of N-acetyl- and N-glycoloyl-neuraminic acid, and O-(5-acetamido-3,5-dideoxy-D-glycero-α- and β-D-galacto-2-nonulopyranosylonic acid)-(2->6)-O-β-D-galactopyranosyl-(1->4)-D-glucopyranose were regioselectively synthesized by us