88713-85-3

Upstream product

• 71454-40-5 Methyl 2,3,6-tri-O-benzyl-4-O-(methanesulfonyl)-α-D-galactopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 87871-03-2 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethanesulfonyl-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 1093187-69-9 1-C-(4-azido-2,3,6-tri-O-benzyl-1,4-dideoxy-α-D-galactopyranosyl)propene 
• 88714-23-2 C₂₄H₂₇N₃O₇ 
• 1430222-68-6 C₂₅H₂₉N₃O₅ 
• 1422964-65-5 C₂₄H₂₉N₃O₇S 
• 1422964-77-9 C₂₃H₂₅N₃O₄ 
• 1422964-64-4 2-C-(6-iodo-2,3-di-O-benzyl-4-azido-4,6-dideoxy-α-D-galactopyranosyl)acetone 
• 172297-88-0 methyl 2,3,6-tri-O-benzyl-4-deoxy-β-L-threo-hex-4-enopyranoside 
• 88713-90-0 4-azido-2,3,6-tri-O-benzyl-4-deoxy-D-galactono-1,5-lactone 

Relevant academic research and scientific papers

Quantifying the electronic effects of carbohydrate hydroxy groups by using aminosugar models

Methyl amino-deoxy-glycosides with α- and β-gluco, α-galacto, or α-manno stereochemistry with the amino functionality in each of the four possible non-anomeric positions have been synthesized and their pKa values determined by titration. These

Synthesis of iminoalditol analogues of galactofuranosides and their activities against glycosidases

Iminoalditol analogues of galactofuranosides were synthesized from 1-C-(2′-oxo-propyl)-1,4-dideoxy-1,4-imino-d-galactosides and different amines by reductive amination, followed by removal of protecting groups. The activity of these compounds against galactosidases and other glycosidases was investigated. The best inhibitor against β-galactosidase (bovine liver) is a diastereomeric mixture of an iminoalditol (10h), which contains a hydrophobic hexadecyl aglycon (R = C16H33), whereas no significant inhibitory activity was observed with compounds having a hydrophilic aglycon. Surprisingly, activation of α-galactosidase (coffee bean) by 10h was also observed. Because these results were obtained from a mixture of iminoalditols, the inhibition and activation of glycosidases could result from different diastereomers. Crown Copyright

Application of the Synthetic Aminosugars for Glycodiversification: Synthesis and Antimicrobial Studies of Pyranmycin

A divergent approach was employed for the synthesis of aminosugars, from which a novel library of aminoglycoside antibiotics (pyranmycins) was synthesized. Pyranmycins have comparable antibacterial activity as neomycin, a clinically used aminoglycoside antibiotic, against Escherichia coli, Staphylococcus aureus, Bacillus subtilis, and Mycobacterium smegmatis. In addition, pyranmycins, like streptomycin, are bacteriocidal while isoniazid (INH) is bacteriostatic. Therefore, pyranmycins may provide new therapeutic options in the treatment against tuberculosis. Several members of pyranmycins also manifest modest anti-Tat and anti-Rev activities, which may aid in the development of new anti-HIV agents. Although the antibacterial activity of pyranmycins against aminoglycoside resistant bacteria is less than expected, the synthetic methodologies of utilizing a library of aminosugars can be a model for future studies of glycodiversification or glycorandomization.

SYNTHESIS OF METHYL 2,3-O-D-GLYCOPYRANOSYLIDENE α-D-MANNOPYRANOSIDES HAVING VARIOUS SUBSTITUENTS

The title compounds were obtained by condensation of D-glucono-, D-galactono-, or L-glycero-D-gluco-heptono-1,5-lactones with methyl 2,3-di-O-(trimethylsilyl)-α-D-mannopyranosides having various substituents on C-4 and C-6, in the presence of trimethylsil