128678-36-4

Basic information

• Product Name: Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• Synonyms: Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate
• CAS NO: 128678-36-4
• Molecular Weight: 567.547
• Mol File: 128678-36-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(128678-36-4)
• EPA Substance Registry System: Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate(128678-36-4)

Safety Data

• Hazardous Substances Data: 128678-36-4(Hazardous Substances Data)

Upstream product

• 84380-10-9 4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester 
• 108-95-2 phenol 
• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 6931-68-6 methyl 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 
• 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

• 15964-32-6 (Phenyl 5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onic 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.

PHASE-TRANSFER-CATALYZED SYNTHESIS OF ARYL α-KETOSIDES OF N-ACETYLNEURAMINIC ACID. A 2-METHYLFLUORAN-6-YL GLYCOSIDE OF N-ACETYLNEURAMINIC ACID, 2-METHYL-6-(5-ACETAMIDO-3,5-DIDEOXY-α-D-glycero-D-galacto-NONULOPYRANOSYLONIC ACID)XANTHENE-9-SPIRO-1'-ISOBENZOFURAN-3'-ONE, A NEW SUBSTRATE..

Glycosidation of N-acetylneuraminic acid by phase-transfer catalysis in chloroform-aqueous alkali gave several known and some new aryl α-ketosides in a short reaction time and in good yields.The 4-methylumbelliferyl α-ketoside, the standard substrate for neuraminidase, was prepared in a yield of up to 70percent.New Neu5Ac ketosides were prepared with fluorescein and the fluorescein analog, 2-methyl-6-hydroxyfluoran (2-methyl-6-hydroxyxanthene-9-spiro-1'-isobenzofuran-3'-one) as aglycons, the latter being synthesized from 2-(2-hydroxy-5-methylbenzoyl) benzoic acid and 3-fluorophenol.The α configuration was ascertained by 400-MHz 1H-NMR spectroscopy and by cleavage of the ketosides with neuraminidases from Vibrio cholerae and Clostridium perfringens.The enzymic hydrolysis of the 2-methylfluoran-6-yl ketoside gave Km values of 82 μM (V. cholerae) and 96 μM (C. perfringens).