866332-40-3

Upstream product

• 374573-40-7 (2S,4S,5R,6R)-5-Amino-4-hydroxy-2-p-tolylsulfanyl-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108-24-7 acetic anhydride 
• 862851-24-9 methyl (4-methylphenyl 3,5-dideoxy-2-thio-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 

Downstream Products

• 866332-54-9 C₅₂H₆₁F₆N₂O₂₆P 
• 866332-47-0 methyl 4,7,8-tri-O-acetyl-3,5-dideoxy-2-(4-methylphenylthio)-9-O-(methyl-5-trifluoroacetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosylonate)-5-trifluoroacetamido-D-glycero-α-D-galacto-non-2-ulopyranosidonate 
• 866332-39-0 C₄₃H₅₂F₆N₂O₂₂S 
• 866332-36-7 (2S,4S,5R,6R)-4-Acetoxy-6-((1R,2R)-1-acetoxy-2,3-dihydroxy-propyl)-2-p-tolylsulfanyl-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Phosphite-based sialic acid donors in the synthesis of α(2→9) oligosialic acids

The combination of a phosphite donor and an anomeric thiocresol-protected acceptor, both with a TFA protecting group at C-5 of the sialic acid, provides good α-selectivity and yield in sialylation. Although the convergent synthetic strategy of using a phosphite disialo-donor and a disialo-acceptor assembles tetra-sialic acid efficiently, overcoming the low α-selectivity of α-anomer and purifying it remain to be achieved. Furthermore, mono- and di-sialic acids were, respectively, conjugated on carrier protein, keyhole limpet hemocyanin. The enzymatic hydrolysis method is recommended for estimating the amount of sialic acid on a protein conjugate.

N-trifluoroacetyl sialyl phosphite donors for the synthesis of α(2 → 9) oligosialic acids

(Chemical Equation Presented) A new method for the synthesis of α(2 → 9) oligosialic acids is developed using phosphite sialyl donors that are protected with a C-5 N-trifluoroacetyl (NHTFA) substituent. Compared with conventional donors, these donors gave a higher degree of α-anomeric selectivity during glycosidic bond formation and better yields during iterative sialylation in the synthesis of oligosialic acids.