1246533-58-3

Upstream product

• 1235555-29-9 methyl (4-methylphenyl 5-amino-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate 
• 75-36-5 acetyl chloride 
• 106-45-6 para-thiocresol 
• 1071226-27-1 methyl (2-p-methylphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-D-glycero-α/β-D-galacto-2-thio-nonulopyranosid)onate 
• 20298-35-5 N-acetylneuraminic 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 
• 1235555-31-3 methyl (4-methylphenyl 5-amino-5-N,4-O-carbonyl-3,5-dideoxy-2-thio-D-glycero-β-D-galacto-non-2-ulopyranoside)onate 

Downstream Products

• 1590365-50-6 methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 
• 1590365-52-8 methyl (cyclohexyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galacto-non-2-ulopyranoside) onate 
• 934592-21-9 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galactonon-2-ulopyranosylonate-(2->3)-methyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 934591-89-6 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-β-D-galactonon-2-ulopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 934592-18-4 methyl 5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ylopyranosylonate-(2->6)-methyl 2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 1359855-60-9 methyl (2-C-(2-oxo-2-phenylethyl)-5-N-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranitol)onate 
• 1345019-98-8 C₅₃H₅₃NO₂₀S 
• 1385027-83-7 C₁₉H₂₃NO₁₂ 
• 1246533-65-2 C₃₉H₄₅NO₁₇S 
• 1345020-10-1 C₄₂H₅₄N₂O₂₂S 
• 1345020-09-8 C₄₆H₄₉NO₁₉S 
• 1345020-07-6 C₄₂H₄₇Cl₃N₂O₁₈S 
• 1345020-08-7 C₃₅H₄₅NO₁₇S 

Relevant academic research and scientific papers

Donor-Reactivity-Controlled Sialylation Reactions

Although tremendous efforts have been made for the efficient preparation of sialosides, controlling the stereochemical outcome of sialylation reaction still remains one of the most challenging tasks due to the unique chemical structure of sialic acid. We developed a new strategy to statistically analyze the stereoselectivity of sialylation reactions on six types of p-tolyl thiosialosides in NIS/TfOH system using Relative Reactivity Value (RRV) as the indicator. Analysis of the reaction mechanism showed the formation of the relatively stable glycosyl bromide and glycosyl chloride intermediates from halide- and triflate-containing promotors in the absence of an acceptor. We found that the α/β-stereoselectivity, yields, and intermediate changes were associated with their donor reactivity. These findings enable to tailor the most suitable building blocks for stereo-controlled sialylation reactions.

Comparative studies on the O-sialylation with four different α/β-oriented (N-acetyl)-5-N,4-O-carbonyl-protected p-toluenethiosialosides as donors

Four types of 5-N,4-O-carbonyl-protected p-toluenethiosialosides were synthesized and their couplings with different acceptors were thoroughly investigated. The results indicate that the sialyl donor structure, the amount of glycosyl acceptor, and the detailed promotion conditions have great influence on the sialylation stereoselectivties and product yields. Under the (p-Tol)2SO/Tf2O activation conditions, the glycosylations with simple alcohols provided declined α-selectivities and higher yields with increasing the amounts of acceptors from 1.1 equiv to 2.0 equiv. However, the outcome of same sialylation was independent of the relative amounts of sugar alcohol acceptors. With NIS/TfOH as promoter, the α-selectivities of the sialylations were significantly improved compared with the cases activated by (p-Tol)2SO/Tf2O. In general, the difference in configuration of N-acetylated sialyl donors (D2 and D4) has little effect on the sialylation yield and stereoselectivity. In contrast, the N-deacetylated α/β sialyl donors (D1 and D3) show complex sialylation profiles with different acceptors.