133004-71-4

Upstream product

• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 75-05-8 acetonitrile 
• 131531-76-5 p-methylphenyl 2,3,4,6-tetra-O-benzyl-thio-β-D-glucopyranoside 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 

Downstream Products

• 132884-68-5 N-<1-benzyl N-(tert-butyloxycarbonyl)-4-L-aspartyl>-2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine 
• 193154-32-4 Acetic acid (2R,3R,4S,5S,6S)-6-((2R,3R,4S,5R,6R)-3-acetoxy-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylcarbamoyl)-4,5-bis-benzyloxy-2-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-3-yl ester 
• 77611-19-9 2-O-Acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosylamine 

Relevant academic research and scientific papers

A practical synthesis of various 2-deoxy-N-glycosides by using D-glucal

We herein report the synthesis of 2-deoxy-2-iodo-glycosylamides, glycosylurea, N-glycosylbenzotriazole, and N-glycosyl imidazole by addition reaction of trimethylsilyl amides, imidazoles, and benzotriazoles to D-glucal in the presence of N-iodosuccinimide and propionitrile at 0 C. Two diastereomers were isolated - the α-mannose and β-gluco isomers. Reduction and substitution reaction of the iodine at position C-2 led to formation of various 2-deoxy-N-glycosides and 2-hydroxy-β-D-glucopyranosylamide. The newly generated compounds were screened for their inhibitory activity against various enzymes that included Nav1.7 sodium ion voltage-gated channel in HEK293 cells and the results are discussed.

Neighboring-group participation by C-2 ether functions in glycosylations directed by nitrile solvents

Ether-protecting functions at C-2 hydroxy groups have been found to play participating roles in glycosylations when the reactions are conducted in nitrile solvent mixtures. The participation mechanism is based on intramolecular interaction between the lone electron pair of the oxygen atom of the C-2 ether function and the nitrile molecule when they are positioned in a cis configuration. A 1,2-cis glycosyl oxazolinium intermediate is formed. This participation, in conjunction with the anomeric effect of the glycosyl donor, confers high 1,2-trans selectivities on glycosylations. Further application of this concept has led to efficient preparations of α-(1→5)-arabinan oligomers.

Synthesis and biological evaluation of a backbone-modified phytoalexin elicitor

Two suitably protected building blocks (11 and 33) for the preparation of amide-linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal