148416-93-7

Upstream product

• 84278-00-2 1,3,4,6-tetra-O-acetyl-2-azido-2-deoxy-D-galactopyranose 
• 108-98-5 thiophenol 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-D-galactopyranosyl chloride 
• 4098-06-0 triacetyl-D-galactal 
• 882-33-7 diphenyldisulfane 
• 14204-27-4 N-phenylthiophthalimide 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 

Downstream Products

• 500212-92-0 phenyl 2-azido-6-O-(tert-butyldiphenylsilyl)-2-deoxy-1-thio-α-D-galactopyranoside 
• 500213-00-3 phenyl 2-azido-4,6-O-benzylidene-2-deoxy-1-thio-α-D-galactopyranoside 
• 13992-16-0 1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose 

Relevant academic research and scientific papers

A study of the mechanism of the azidophenylselenylation of glycals

Chemical and physicochemical studies of homogeneous azidophenylselenylation of glycols with diacetoxyiodobenzene, trimethylsilyl azide, and diphenyl diselenide in dichloromethane revealed that the most probable key reaction step is the formation of phenylselenyl azide, an azide radical donor. A method for azidophenylsulfenylation of glycals was proposed.

Cytotoxic properties of d-gluco-, d-galacto- and d-manno-configured 2-amino-2-deoxy-glycerolipids against epithelial cancer cell lines and BT-474 breast cancer stem cells

Glycosylated antitumor ether lipids (GAELs) 6 and 7 containing a α- or β-d-gluco-configured 2-amino-2-deoxy (2-NH2-Glc) sugar moiety linked to a glycerolipid aglycone kill cancer cell lines via a non-apoptotic mechanism that could be exploited

Selectin Inhibitors, Composition, and Uses Related Thereto

This disclosure relates to selectin inhibitors, compositions, and methods related thereto. In certain embodiments, the disclosure relates to glycopeptides that contain one more modified amino acids conjugated to a saccharide or polysaccharide. In certain

Synthesis of the repeating unit of the lipoteichoic acid of Streptococcus pneumoniae

The lipoteichoic acid repeating unit of Streptococcus pneumoniae is a complex pseudopentasaccharide (3). It consists of one ribitol-phosphate, one 2-acetamino-4-amino-2,4,6-trideoxy-galactose, one glucose and two galactosamine residues each differently li

An improved method for the synthesis of protected glycosyl fluorides from thioglycosides using N,N-diethylaminosulfur trifluoride (DAST)

The direct conversion of thioglycosides to glycosyl fluorides frequently used in oligosaccharide synthesis was examined using N,N-diethylaminosulfur trifluoride (DAST). Although the reaction proceeded without N-bromosuccinimide (NBS), in some cases it was found that the electrophilicity of the Vilsmeier-type electrophilic sulfinium cation species was not sufficient for the activation of certain less-reactive thioglycosides. Here, we report the results of fluorination reactions of a series of monosaccharides using DAST in the absence of NBS, and also discuss the acceleration of the reaction in the presence of dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) resulting in excellent product yields.

Syntheses of α- and β-glycosyl donors with a disaccharide β-D-Gal-(1→3)-D-GalNAc backbone

The synthesis of thioglycoside glycosyl donors with a disaccharide β-D-Gal-(1 → 3)-D-GalNAc backbone was studied using the glycosylation of a series of suitably protected 3-monohydroxy- and 3,4-dihydroxyderivatives of phenyl 2-azido-2-deoxy-1-thio-α- and 1-thio-β -D-galactopyranosides by galactosyl bromide, fluoride, and trichloroacetimidate. In the reaction with the monohydroxylated glycosyl acceptor, the process of intermolecular transfer of thiophenyl group from the glycosyl acceptor onto the cation formed from the molecule of glycosyl donor dominated. When glycosylating 3,4-diol under the same conditions, the product of the thiophenyl group transfer dominated or the undesired (1 → 4), rather than (1 → 3)-linked, disaccharide product formed. The aglycon transfer was excluded when 4-nitrophenylthio group was substituted for phenylthio group in the galactosyl acceptor molecule. This led to the target disaccharide, 4-nitrophenyl 2-azido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β -D-galactopyranosyl)-1-thio-β-D-galactopyranoside, in 57% yield. This disaccharide product bears nonparticipating azido group in position 2 of galactosamine and can hence be used to form α-glycoside bond. Azido group and the aglycon nitro group were simultaneously reduced in this product and then trichloroacetylated, which led to the β-glycosyl donor, 4-trichloroacetamidophenyl 4,6-di-O-acetyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) -1-thio-2-trichloroace-tamido-β-D-galactopyranoside, in 62% yield. The resulting glycosyl donor was used in the synthesis of tetrasaccharide asialo-GM1.

Synthesis of Tn, sialyl Tn and HIV-1-derived peptide antigen conjugates having a lipid a analog as an immunoadjuvant for synthetic vaccines

Conjugates (3-5) of Tn, sialyl Tn and HIV-1-derived peptide antigen with a N-tetradecanoyl L-serine-β-alanine-containing D-glucosamine derivative, structurally related to lipid A, as an immunoadjuvant for the development of totally synthetic vaccines against cancers or HIV were synthesized. The mitogenic activity of compounds 3, 4 and 5 was stronger than that of lipid A analogs (1, 2).