87871-04-3

Upstream product

• 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 
• 100-39-0 benzyl bromide 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 7177-79-9 methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 methyl 4,6-O-benzylidene-α-D-glucopyranoside 
• 160533-92-6 methyl 2,3,6-tri-O-benzyl-4-O-(methylthio)thiocarbonyl-α-D-glucopyranoside 
• 87871-03-2 methyl 2,3,6-tri-O-benzyl-4-deoxy-4-trifluoromethanesulfonyl-α-D-glucopyranoside 

Downstream Products

• 190910-34-0 2,3,6-tri-O-benzyl-4-deoxy-5-O-tert-butyldimethylsilyl-D-xylo-hexose N,N-dimethylhydrazone 
• 190910-35-1 2,3,6-tri-O-benzyl-4-deoxy-5-O-(tert-butyldimethylsilyl)-D-xylo-hexonic acid 
• 190910-32-8 2,3,6-tri-O-benzyl4-deoxy-5-O-(tert-butyldiphenylsilyl)-D-xylo-hexose 
• 190910-33-9 2,3,6-tri-O-benzyl-4-deoxy-D-xylo-hexose N,N-dimethylhydrazone 
• 87871-05-4 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-α-D-<4-2H>galactopyranoside 

Relevant academic research and scientific papers

Assessing the Optimal Deoxygenation Pattern of Dodecyl Glycosides for Antimicrobial Activity Against Bacillus anthracis

The discovery of the bactericide dodecyl 2,6-dideoxypyranoside reorganizing membrane phospholipid matrix of Bacillus species into a hexagonal phase, encouraged further research on glycone deoxygenation/bioactivity relationship. We now describe expedient syntheses of new 2-, 3-, 4-deoxy, 2,3- and 3,4-dideoxy glycosides in moderate to good yields. Interestingly, Amberlyst 15 is a key protagonist, efficiently applied for the transacetalation of alkyl deoxy glycosides and for ring contraction to access regioselectively hexofuranosides. The 2-deoxy-d-arabino pyranoside affords the higher MIC values against two Bacillus spp. and Enterococcus faecalis, while a 4-fold decrease or higher was found by inversion of configuration or by deoxygenation at C-3. While 2,3- and 3,4-dideoxygenation do not improve bioactivity, the 4,6-dideoxy-α-d-xylo-hexopyranoside remains a promising glycoside, presenting low MIC values for all species tested, and low cytotoxicity in intestinal and liver cell models.

Synthesis of double-chain bis-sulfone neoglycolipids of the 2''-, 3''-, 4''-, and 6''-deoxyglobotrioses

2-(Trimethylsilyl)ethyl (Me3SiCH2CH2) 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-benzoyl-6-O-p-methoxybenzyl-β-D-galactopyranosyl-β-D-glucopyranoside was glycosylated with different 2-, 3-, 4-, or 6-"deoxy-D-galactose" derivatives to give the corresponding deoxytr