19488-41-6

Usage

Uses

Used in Biochemical Research:
Methyl 2,3,6-Tri-O-benzoyl-4-deoxy-a-D-glucopyranoside is used as a substrate molecule for studying the substrate specificity of certain transferase enzymes involved in glycoprotein biosynthesis. This application is crucial for understanding the mechanisms of protein glycosylation, which plays a vital role in various biological processes and has implications in the development of therapeutic strategies for diseases related to glycosylation abnormalities.
Used in Pharmaceutical Development:
Methyl 2,3,6-Tri-O-benzoyl-4-deoxy-a-D-glucopyranoside is also used to investigate the epitope binding of particular murine monoclonal antibodies. This research is essential for the development of targeted therapies and diagnostic tools in the pharmaceutical industry, as monoclonal antibodies have become a cornerstone in the treatment of various diseases, including cancer and autoimmune disorders.

InChI:InChI=1/C28H26O8/c1-32-28-24(36-27(31)21-15-9-4-10-16-21)23(35-26(30)20-13-7-3-8-14-20)17-22(34-28)18-33-25(29)19-11-5-2-6-12-19/h2-16,22-24,28H,17-18H2,1H3/t22?,23-,24-,28-/m0/s1

Upstream product

• 13264-02-3 methyl 2,3,6-tri-O-benzoyl-4-S-cyano-4-thio-α-D-glucopyranoside 
• 23487-07-2 methyl 2,3,6-tri-O-benzoyl-4-deoxy-4-iodo-α-D-gluco-pyranoside 
• 124314-29-0 methyl 2,3,6-tri-O-benzoyl-4-deoxy-β-D-xylo-hexopyranoside 
• 79233-80-0 methyl 2,3,6-tri-O-benzoyl-4-O-(imidazol-1-ylthiocarbonyl)-α-D-galactopyranoside 
• 141020-13-5 Methyl-2,3,6-tri-O-benzoyl-4-O-phenoxythiocarbonyl-α-D-galactopyranosid 
• 107-13-1 acrylonitrile 
• 79233-81-1 methyl 2,3,6-tri-O-benzoyl-4-O-(imidazolylthiocarbonyl)-α-D-glucopyranoside 
• 149832-00-8 C₃₀H₂₈O₉S₂ 
• 264610-67-5 C₃₅H₃₀O₁₀S 
• 3601-36-3 methyl 2,3,6-tri-O-benzoyl-α-D-galactopyranoside 
• 4137-34-2 methyl 2,3,6-tri-O-benzoyl-4-O-methylsulphonyl-α-D-galactopyranoside 
• 118868-79-4 methyl 4-S-acetyl-2,3,6-tri-O-benzoyl-4-thio-α-D-galactopyranoside 
• 688-73-3 tri-n-butyl-tin hydride 
• 98-88-4 benzoyl chloride 

Downstream Products

• 141020-15-7 2,3,6-Tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranosyliodid 
• 141020-14-6 1-O-Acetyl-2,3,6-tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranose 
• 151073-10-8 2,3,6-Tri-O-benzoyl-4-desoxy-D-xylo-hexose 
• 141020-19-1 Benzyl-O-(4-desoxy-β-D-xylo-hexopyranosyl)-(1->3)-2-acetamido-2-desoxy-α-D-galactopyranosid 
• 141020-16-8 O-(2,3,6-Tri-O-benzoyl-4-desoxy-β-D-xylo-hexopyranosyl)trichloroacetamidat 
• 141020-18-0 Benzyl-O-(2,3,6-tri-O-benzoyl-4-desoxy-β-D-xylo-hexopyranosyl)-(1->3)-2-acetamido-4,6-di-O-acetyl-2-desoxy-α-D-galactopyranosid 
• 141020-17-9 Benzyl-O-(2,3,6-tri-O-benzoyl-4-desoxy-β-D-xylo-hexopyranosyl)-(1->3)-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid 
• 141020-17-9 Benzyl-O-(2,3,6-tri-O-benzoyl-4-desoxy-α-D-xylo-hexopyranosyl)-(1->3)-2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosid 
• 24707-41-3 4-deoxy-D-galactose 
• 5658-14-0 4-deoxy-D-xylo-hexose 
• 114942-44-8 2,4-dinitrophenyl-2,3,6-tri-O-acetyl-4-deoxy-β-D-xylo-hexopyranoside 
• 122714-13-0 1-O-acetyl-2,3,6-tri-O-benzoyl-4-deoxy-β-D-xylo-hexopyranose 
• 149831-92-5 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-O-(5-phthalimidopentyl)-β-D-glucopyranoside 
• 149831-90-3 2-(N-(phenylsulfonyl)indol-3-yl)ethyl 2,3-di-O-benzyl-4-deoxy-6-(O-tert-butyldimethylsilyl)-β-D-glucopyranoside 

Relevant academic research and scientific papers

A One-Pot Method for Removal of Thioacetyl Group via Desulfurization under Ultraviolet Light to Synthesize Deoxyglycosides

We herein developed an efficient method for removing thioacetyl to synthesize acylated deoxy glycosides in a one-pot reaction, where the thioacetyl was selectively deacetylated by hydrazine hydrate in DMF within 2-5 min at room temperature, followed by de

From glycoside hydrolases to thioglycoligases: The synthesis of thioglycosides

The treatment of various glycosyl acceptors, each containing a reactive thiol group, with the appropriate glycosyl donor and a glycoside hydrolase or glycosynthase, failed to yield any thioglycosides - only the products of O-glycosylation were formed. However, thioglycosides were formed when a thioglycoligase was used to mediate the reaction between acceptor and donor. In fact, pyranose acceptors possessing a thiol group at C3, C4 or C6 (but not C2) were all capable of conversion into thioglycosides. Some comment is given regarding the mechanism of the various processes.

Hydrolytic activity of α-galactosidases against deoxy derivatives of p- nitrophenyl α-D-galactopyranoside

The four possible monodeoxy derivatives of p-nitrophenyl (PNP) α-D- galactopyranoside were synthesized, and hydrolytic activities of the α- galactosidase of green coffee bean, Mortierella vinacea and Aspergillus niger against them were elucidated. The 2- and 6-deoxy substrates were hydrolyzed by the enzymes from green coffee bean and M. vinacea, while they scarcely acted on the 3- and 4-deoxy compounds. On the other hand, A. niger α- galactosidase hydrolyzed only the 2-deoxy compound in these deoxy substrates, and the activity was very high. These results indicate that the presence of two hydroxyl groups (OH-3 and -4) is essential for the compounds to act as substrates for the enzymes of green coffee bean and M. vinacea, while the three hydroxyl groups (OH-3, -4, and -6) are necessary for the activity of the A. niger enzyme. The kinetic parameters (K(m) and V(max)) of the enzymes for the hydrolysis of PNP α-D-galactopyranoside and its deoxy derivatives were obtained from kinetic studies. (C) 2000 Elsevier Science Ltd.

NON-PEPTIDE PEPTIDOMIMETICS

Compounds are provided which are crossreactive with peptides such as those which bind G-protein-linked receptors, together with preparative and therapeutic methods therefor. The compounds have the general structure: STR1 wherein at least one of R 1, R 2, R. sub.3, R. sub.4, or R 5 comprises a functional group which is chemically similar to that found in the peptide of interest.

Synthesis of methyl O-α-L-rhamnopyranosyl-(12)-α-D-galactopyranosides specifically deoxygenated at position 3, 4, or 6 of the galactose residue

The title disaccharides were synthesized by condensation of 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide with suitably protected, deoxygenated derivatives of methyl α-D-galactopyranoside.Deoxygenation was achieved via activation of a protected methyl α

De novo design and synthesis of somatostatin non-peptide peptidomimetics utilizing β-D-glucose as a novel scaffolding

Non-peptide peptidomimetics of the peptide hormone somatostatin (SRIF) were designed and synthesized, utilizing β-D-glucose as a novel scaffolding. Such compounds resemble conventional peptide analogs in that they retain critical amino acid side chains bu

Building Units of Oligosaccharides, CIII. - Synthesis of Modified Derivatives of the Disaccharide β-D-Gal-(1->3)-α-D-GalNAc for the Examination of Substrate Specifities of Core 2-β6-GlcNAc-Transferase and α-3-Sialyltransferase Involved in the Biosynthesis

Derivatives of benzyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside have been synthesized.The 6'-, 4'- and 3'-OH group of the galactose moiety as well as the 6- and 4-OH and the 2-acetamido group of the 2-acetamido-2-deoxy-D-galact

Synthesis of specifically deoxygenated ligands related to (1->6)-β-D-galacto-oligosaccharides, and studies on their binding to monoclonal antigalactan antibodies

Synthetic deoxygenated derivatives of methyl β-glycosides of (1->6)-β-D-galacto-oligosaccharides were prepared, and their binding to antigalactan monoclonal antibodies X24 and J539 (Fab') was studied.The results suggest the involvement of an additional, critical hydrogen bond in the highest affinity subsite (A), which now appears to require two hydrogen bonds from the 2- and 3-hydroxyls of the galactosyl residue to the protein, and one from the protein to O-4 of that residue.The data obtained with a series of oligosaccharides deoxygenated at position 31, 32,33, 41, 42, or 43 support the binding patterns and subsite-arrangement inferred previously from studies with large numbers of deoxyfluoro-substituted ligands and this family of antibodies.