439595-86-5

Upstream product

• 103-82-2 phenylacetic acid 
• 13992-25-1 1-azido-1-deoxy-β-D-glucopyranoside tetraacetate 
• 103-80-0 phenylacetyl chloride 
• 20379-61-7 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl azide 
• 525589-11-1 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)[2,1-d]-2-oxazoline 
• 23776-85-4 N-(phenylacetyl)oxysuccinimide 
• 61049-78-3 S-pyridin-2-yl 2-phenylethanethioate 

Relevant academic research and scientific papers

Stereoselective synthesis of α- and β-glycosylamide derivatives from glycopyranosyl azides via isoxazoline intermediates

Treatment of 2-acetoxy glycopyranosyl azides with Ph3P gave isoxazolines by ring closure of the phosphorimine. Coupling of in situ generated isoxazolines with acylating reagents gave mixtures of α- or β-glycopyranosyl amides. The α/β ratio depe

Synthesis of Glycosyl Amides Using Selenocarboxylates as Traceless Reagents for Amide Bond Formation

Carbohydrate-derived amides were successfully prepared in good yields from a broad range of substrates, including furanosyl and pyranosyl derivatives. The methodology successfully relied on the in situ generation of lithium selenocarboxylates from Se/LiEt3BH and acyl chlorides or carboxylic acids and their reaction with sugar azides. A key aspect of the present protocol is that we start from elemental selenium; isolation and handling of all reactive and sensitive selenium-containing intermediates is avoided, therefore providing the selenocarboxylate the status of a traceless reagent.

Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy- β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase

2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl- and 2-acetamido-3,4,6-tri- O-acetyl-2-deoxy-β-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(β-D-glycopyranosyl) amides via a PMe 3 mediated Staudinger protocol (ge