765952-64-5

Upstream product

• 100-39-0 benzyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 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 
• 98-88-4 benzoyl chloride 
• 303127-81-3 p-methoxyphenyl 3-O-benzyl-4,6-di-O-benzylidene-β-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 774591-92-3 4-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 774591-90-1 4-methoxyphenyl 2,3,6-tri-O-benzyl-4-O-(6-O-benzyl-4-deoxy-4-azido-β-D-galactopyranosyl)-β-D-glucopyranoside 
• 774591-94-5 4-methoxyphenyl (3,4-di-O-acetyl-4-azido-6-O-benzyl-4-deoxy-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 774591-89-8 4-methoxyphenyl (6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 774591-93-4 4-methoxyphenyl (3,4-di-O-acetyl-6-O-benzyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-galactopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside 
• 1448540-27-9 4-O-acetyl-2,3-di-O-benzoyl-6-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate 
• 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 
• 1448540-30-4 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 
• 1200878-78-9 p-methoxyphenyl 2,3-di-O-benzoyl-β-D-glucopyranoside 
• 1381876-01-2 p-methoxyphenyl 2,3-di-O-benzoyl-6-O-levulinoyl-β-D-glucopyranoside 

Relevant academic research and scientific papers

Total Synthesis of the Phosphorylated Zwitterionic Trisaccharide Repeating Unit of Photorhabdus temperata cinerea 3240

Herein, we report the total synthesis of the phosphorylated zwitterionic trisaccharide repeating unit of Photorhabdus temperata subsp. cinerea 3240. The efficient route involves regio- and stereoselective assembly of trisaccharide with rare deoxyamino sug

Is an acyl group at O-3 in glucosyl donors able to control α-stereoselectivity of glycosylation? the role of conformational mobility and the protecting group at O-6

The stereodirecting effect of a 3-O-acetyl protecting group, which is potentially capable of the remote anchimeric participation, and other protecting groups in 2-O-benzyl glucosyl donors with flexible and rigid conformations has been investigated. To this aim, an array of N-phenyltrifluoroacetimidoyl and sulfoxide donors bearing either 3-O-acetyl or 3-O-benzyl groups in combination with 4,6-di-O-benzyl, 6-O-acyl-4-O-benzyl, or 4,6-O-benzylidene protecting groups was prepared. The conformationally flexible 3-O-acetylated glucosyl donor protected at other positions with O-benzyl groups demonstrated very low or no α-stereoselectivity upon glycosylation of primary or secondary acceptors. On the contrary, 3,6-di-O-acylated glucosyl donors proved to be highly α-stereoselective as well as the donor having a single potentially participating acetyl group at O-6. The 3,6-di-O-acylated donor was shown to be the best α-glucosylating block for the primary acceptor, whereas the best α-selectivity of glycosylation of the secondary acceptor was achieved with the 6-O-acylated donor. Glycosylation of the secondary acceptor with the conformationally constrained 3-O-acetyl-4,6-O-benzylidene-protected donor displayed under standard conditions (-35 C) even lower α-selectivity as compared to the 3-O-benzyl analogue. However, increasing the reaction temperature essentially raised the α-stereoselectivities of glycosylation with both 3-O-acetyl and 3-O-benzyl donors and made them almost equal. The stereodirecting effects of protecting groups observed for N- phenyltrifluoroacetimidoyl donors were also generally proven for sulfoxide donors.2013 Elsevier Ltd. All rights reserved.

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.

Interhalogens (ICl/IBr) and AgOTf in thioglycoside activation; synthesis of bislactam analogues of ganglioside GD3

The novel promoter system IX/AgOTf (X = Cl or Br) has been evaluated in the synthesis of two bislactam analogues of GD3. We have carried out two high-yielding galactosylations in 97% and 98% yield, respectively, using ICl/AgOTf, and four sialylations in 9