884654-97-1

Upstream product

• 98056-57-6 methyl 2,4,6-tri-O-benzoyl-β-D-galactopyranoside 
• 98056-58-7 2,4,6-tri-O-benzoyl-3-O-benzyl-α-D-galactopyranosyl chloride 
• 86520-52-7 2-[2-(2-azidoethoxy)ethoxy]ethanol 
• 5197-62-6 2-[2-(chloroethoxy)ethoxy]ethanol 
• 884654-92-6 2-[2-(2-azidoethoxy)ethoxy]ethyl 2,4,6-tri-O-benzoyl-3-O-benzyl-β-D-galactopyranoside 

Downstream Products

• 884655-01-0 2-[2-(2-azidoethoxy)ethoxy]ethyl 3-O-benzyl-2-O-(2,4-di-O-benzyl-3,6-dideoxy-α-L-xylo-hexopyranosyl)-β-D-galactopyranoside cyclic [P(R)]-4,6-(2,2,2-trichloroethyl phosphate) 

Relevant academic research and scientific papers

Synthesis of a phosphorylated disaccharide fragment of the O-specific polysaccharide of Vibrio cholerae O139, functionalized for conjugation

The title disaccharide, 2-(2-(2-[(2-ethoxy-3,4-dioxocyclobut-1-en-1-yl) amino]ethoxy}ethoxy}ethyl 2-O-(3,6-dideoxy-α-L-xylo-hexopyranosyl)-β- D-galactopyranoside cyclic 4,6-(potassium phosphate) (2), was synthesized from the two isomeric linker-equipped galactose acceptors 9 and 10, obtained by phosphorylation of 2-[2-(2-azidoethoxy)ethoxy]ethyl 3-O-benzyl-β-D- galactopyranoside (8). which were glycosylated with ethyl 2,4-di-O-benzyl-3,6- dideoxy-1-thio-β-L-xylo-hexopyranoside (12; Scheme). Mainly the fully protected α-(1 → 2)-linked products 13a and 14a were formed. Catalytic hydrogenolysis/hydrogenation effected global deprotection, thereby removing the chirality at the P-atom. and simultaneously converted the azido group in the linker to an amino group (→15). Final treatment with diethyl squarate (=3,4-diethoxycyclobut-3-ene-1,2-dione) gave target compound 2, amenable for conjugation to proteins.