59694-37-0

Basic information

• Product Name: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• Synonyms: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• CAS NO: 59694-37-0
• Molecular Weight: 612.544
• Mol File: 59694-37-0.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(59694-37-0)
• EPA Substance Registry System: methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(59694-37-0)

Safety Data

• Hazardous Substances Data: 59694-37-0(Hazardous Substances Data)

Upstream product

• 100-02-7 4-nitro-phenol 
• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 19342-33-7 N-acetyl neuraminic acid 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 251941-09-0 methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-α-D-erythro-L-gluco-2-nonulopyranosid)onate 
• 824-78-2 4-nitrophenol sodium salt 
• 109681-08-5 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-bromo-2,5-dideoxy-D-erythro-α-L-gluco-non-2-ulopyranosonate 
• 294183-03-2 methyl (p-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-5-deoxy-3-O-(phenoxythiocarbonyl)-α-D-erythro-L-gluco-2-nonulopyranosid)onate 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 6770-41-8 Methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-β-D-glycero-D-galacto-2-nonulopyranosyl chloride)onate 

Downstream Products

• 1227297-22-4 methyl [(4-nitrophenyl) 4,7,8,9-tetra-O-acetyl-5-(1-methoxyethylideneamino)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 
• 134136-43-9 7-N-<4-O-(Methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didedoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)phenyl>-9a-methoxymitosane 
• 134136-44-0 7-N-<4-O-(Methyl 5-acetamido-3,5-didedoxy-α-D-glycero-D-galacto-2-nonulopyranosylonate)phenyl>-9a-methoxymitosane 
• 143857-99-2 (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-(4-acryloylamino-phenoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 143858-01-9 (2S,4S,5R,6R)-5-Acetylamino-2-(4-acryloylamino-phenoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid 
• 59694-35-8 methyl <(4-nitrophenyl) 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid>onate 
• 130087-26-2 methyl (4-aminophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 26112-88-9 2-O-(p-nitrophenyl)-5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-nonulopyranusonic acid 

Relevant articles and documents

Glycosylation with ulosonates under Mitsunobu conditions: Scope and limitations

A systematic study was performed by using Mitsunobu conditions (diethyl azodicarboxylate, Ph3P or n-Bu3P in THF or CH3CN) for glycosylations with methyl 3,4,5,7-tetra-O-benzoyl-α-d-gluco-hept-2-ulopyranosonate. From a set of 47 O-, N-, S- and C-nucleophiles, phenols and N-hydroxy compounds with a pKa of 5-8, phthalimide, benzotriazole, 6-chloropurine, an oxazolidinedione and several tetrazoles with a pKa of 4-8, and thiophenol gave the corresponding products in moderate to very good yields, while C-nucleophiles were unreactive. Trihaloacetanilides underwent O-glycosylation to give O-glycosyl-N-aryl trihaloacetimidates which could not be made by conventional O-imidoylations. All reactions were highly stereoselective to produce the β(d) anomers only. With methyl (5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-d-glycero-d-galacto-2-nonulopyranose)onate phenols and benzotriazole resulted in the expected products, but all other nucleophiles failed to react. While these transformations gave anomeric mixtures in a ratio close to 1?:?1 at room temperature, the α-selectivity increased to 92?:?8 at -30 °C. An o-nitrophenyl sialoside was converted to a spiro-benzoxazinone derivative by reduction of the nitro group and subsequent spontaneous ring closure.

Syntheses of C-3-modified sialylglycosides as selective inhibitors of influenza hemagglutinin and neuraminidase

In an effort to develop new structures as inhibitors of both influenza virus proteins hemagglutinin and neuraminidase, a series of sialic acid derivatives, including those with one of the hydrogen atoms at the C-3 position replaced by either OH or F, were synthesized. The sialic acid derivative with a 3-eq-OH group was first synthesized by means of a new process and used as the key intermediate for further derivatization at the C- 3 position. The stability of these compounds under acid- and sialidase- catalyzed hydrolysis conditions was studied, and the results showed that these compounds exhibit stronger resistance towards both conditions than their parent p-nitrophenyl α-sialoside. Further inhibition assay indicated that the 3-ax-OH or F derivatives 4, 5, and 24, the 4-epimer of 4, are effective specific inhibitors of the sialidases from Clostridium perfringens, among other bacterial sialidases tested. The 3-eq-OH derivative 3, however, showed little inhibition. The same tendency was observed for the inhibition of human influenza sialidases N1 and N2. Compounds 3-5 and sialic acid were then converted into the distealoylphosphatidylethanolamine conjugates. Of these liposome-like compounds, the ones from 4 and 5 showed potent and selective inhibitory activities against the hemagglutinin H3 subtype, but displayed resistance to the influenza virus neuraminidases N1 and N2.

Synthese Esterase-bestaendiger, 9-O-acetylierter Polysialoside als Inhibitoren des Influenza-C-Virus-Haemagglutinins

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