87871-03-2

Upstream product

• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 358-23-6 trifluoromethylsulfonic anhydride 
• 1421832-81-6 phenylthio 4,8-anhydro-2,3-di-O-benzyl-6,7-dideoxy-8S-phenyl-α-D-manno-octopyranoside 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 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 
• 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 
• 145100-51-2 N-(5-chloropyridin-2-yl)-1,1,1-trifluoro-N-[(trifluoromethyl)sulphonyl]methanesulphonamide 

Downstream Products

• 87871-04-3 methyl 2,3,6-tri-O-benzyl-4-deoxy-α-D-xylo-hexopyranoside 
• 88713-85-3 methyl 4-azido-2,3,6-tri-O-benzyl-4-deoxy-α-D-galactopyranoside 
• 1387509-48-9 methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 
• 1387509-56-9 methyl (2-S-(methyl 2,3,6-tri-O-benzyl-4-thio-α-D-galactopyranoside)-5-N-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 
• 87871-05-4 Methyl 2,3,6-Tri-O-benzyl-4-deoxy-α-D-<4-2H>galactopyranoside 
• 394212-37-4 2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl dibenzyl phosphate 
• 394212-35-2 methyl 2,3,6-tri-O-benzyl-4-S-acetyl-4-thio-α-D-galactopyranoside 
• 19488-48-3 methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside 
• 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 

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.

Influence of O6 in mannosylations using benzylidene protected donors: Stereoelectronic or conformational effects?

The stereoselective synthesis of β-mannosides and the underlying reaction mechanism have been thoroughly studied, and especially the benzylidene-protected mannosides have gained a lot of attention since the corresponding mannosyl triflates often give exce

Highly stereoselective synthesis of primary, secondary, and tertiary α-S-sialosides under lewis acidic conditions

N-Acetyl 4-O,5-N-oxazolidinone protected sialyl phosphates of either anomeric configuration are excellent donors for the formation of α-S-sialosides at -78 °C in dichloromethane with primary, secondary, and tertiary thiols including galactose 3-, 4-, and

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

The first synthesis of secondary sugar sulfonic acids by nucleophilic displacement reactions

The 4-deoxy-4-C-sulfonic acid and 6-deoxy-6-C-sulfonic acid derivatives of methyl α-D-gluco- and α-D-galactopyranosides were prepared by triflate-mediated nucleophilic displacement reactions, either with NaHSO 3 or with AcSK. The triflate ester

Thiosugar nucleotide analogues: Synthesis of uridine 5′-(2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranosyl diphosphate)

The synthesis of a novel uridine diphosphate galactose (UDP-Gal) analog, (UDP-2,3,6-tri-O-acetyl-4-S-acetyl-4-thio-α-D-galactopyranose) (10) is described. Compound 10 contains a sulfur in the place of oxygen at the 4-position of the galactose moiety. Compound 10 represents a protected form of a novel sugar nucleotide analog that can potentially be used during chemoenzymatic synthesis to modify complex oligosaccharides.

Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases

Disaccharides of 1-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific