1381876-01-2

Upstream product

• 1200878-78-9 p-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranoside 
• 1381875-87-1 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 
• 1381875-99-5 p-methoxyphenyl 2,3-di-O-benzoyl-4-O-levulinoyl-6-O-tert-butyldiphenylsilyl-β-D-glucopyranoside 
• 2872-65-3 p-methoxyphenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 150-76-5 4-methoxy-phenol 
• 3150-20-7 4-methoxyphenyl β-D-glucopyranoside 
• 123-76-2 levulinic acid 
• 765952-64-5 4-methoxyphenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside 
• 604-69-3 β-D-glucose pentaacetate 

Downstream Products

• 1448540-29-1 p-methoxyphenyl 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 
• 1448540-27-9 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 
• 1448540-30-4 p-methoxyphenyl 4,6-di-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 
• 1448540-31-5 4,6-di-O-benzylidene-3-O-chloroacetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1→4)-2,4-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 

Relevant academic research and scientific papers

Synthesis and immunological characterization of modified hyaluronic acid hexasaccharide conjugates

The synthesis of a tetanus toxoid (TT)-conjugate of a hyaluronic acid (HA) hexasaccharide is described. The compound was intended for use in monitoring HA levels as a disease marker and as a potential vaccine against Group A Streptococcus (GAS) infections. We also report the synthesis of a chemically modified HA-hexasaccharide-TT conjugate in which the N-acetyl moiety of the N-acetyl-d-glucosamine residue is replaced with an N-propionyl unit in order to enhance immunogenicity. The oligosaccharides are synthesized in a convergent manner. The TT-conjugate syntheses rely on the reaction of the amines on the 6-aminohexyl aglycon of the hexasaccharides with diethyl squarate to give the monoethyl squarate adducts. Subsequent reactions with lysine ε-amino groups on TT then give the glycoconjugates containing an average of 8 hexasaccharide haptens per TT molecule. Immunological studies in mice show very similar antibody responses with both conjugates, suggesting that the N-acetyl groups of the glucosaminyl residues of the HA-hexasaccharide are not a critical part of the epitope recognized by the anti-HA polyclonal immune response. Furthermore, it would appear that the N-acyl moieties are not in close contact with the amino acid residues of the antibody combining sites.

An efficient and recyclable catalyst for the cleavage of tert-butyldiphenylsilyl ethers

An efficient, chemoselective, and environment-friendly method for the deprotection of tert-butyldiphenylsilyl ethers mediated by triflic acid supported on silica gel is reported. A wide range of tert-butyldiphenylsilyl ethers derived from carbohydrate and saponin residues can be smoothly cleaved in the presence of various types of other protecting groups in good to excellent yields in acetonitrile. This heterogeneous reaction does not require aqueous workup, and the supported catalyst can be readily recycled.