173911-72-3

Upstream product

• 173911-68-7 (2R,4S,5R,6R)-4-Acetoxy-6-[(1R,2R)-1-acetoxy-2-hydroxy-3-(toluene-4-sulfonyloxy)-propyl]-5-acetylamino-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 173911-65-4 (2R,4S,5R,6R)-5-Acetylamino-6-[(1R,2R)-1,2-dihydroxy-3-(toluene-4-sulfonyloxy)-propyl]-4-hydroxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 122777-27-9 Methyl [2-(trimethylsilyl)ethyl 5-acetamido-4,7-di-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid]onate 
• 173911-66-5 (2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-hydroxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 122777-22-4 methyl <2-(trimethylsilyl)ethyl 5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid>onate 
• 98-88-4 benzoyl chloride 
• 156726-99-7 Methyl onate 
• 173911-67-6 (2R,4S,5R,6R)-5-Acetylamino-6-((1R,2R)-3-azido-1,2-dihydroxy-propyl)-4-benzoyloxy-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 173911-70-1 (2R,4S,5R,6R)-4-Acetoxy-6-((1R,2R)-2-acetoxy-3-azido-1-hydroxy-propyl)-5-acetylamino-2-(2-trimethylsilanyl-ethoxy)-tetrahydro-pyran-2-carboxylic acid methyl ester 

Downstream Products

• 173911-74-5 C₃₄H₅₃N₃O₁₅SSi 
• 173911-73-4 methyl (2-(trimethylsilyl)ethyl 5-acetamido-9-azido-3,5,9-trideoxy-8-O-{methyl [5-acetamido-3,5-dideoxy-3-(phenylthio)-D-erythro-α-L-gluco-2-nonulopyranosid]onate}-D-glycero-α-D-galacto-2-nonulopyranosid)onate 

Relevant academic research and scientific papers

Synthesis of a bis(sialic acid) 8,9-lactam

Methyl [2-(trimethylsilyl)ethyl 5-acetamido-9-azido-4-O-benzoyl-3,5,9-trideoxy-D-glycero-α-D-galacto- 2-nonulopyranosid]onate was sialylated with methyl (ethyl 5-acetamido-4,7,8,9-tetra-O-acetyl-2-thio-3-(phenylthio)-2,3,5-trideox y-D-erythro-α-L-gluco-2-nonulopyranosid)onate to give the corresponding bis(sialic acid) derivative in 23% yield. Removal of protecting groups, reduction of the azido group to an amino group, and removal of the auxiliary thiophenyl group gave the desired bis(sialic acid) 8,9-lactam. Comparison of the 1H NMR spectra and energy-minimized (MM3) structures of the bis(sialic acid) lactam with those of the corresponding bis(sialic acid) lactone showed the conformations of the two compounds to be very similar (RMS = 0.027 A).