95530-22-6

Upstream product

• 108-24-7 acetic anhydride 
• 95451-96-0 Allyl-2-azido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranosid 
• 148968-89-2 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-mannopyranose 

Downstream Products

• 95451-97-1 2-Azido-3,4,6-tri-O-benzyl-2-desoxy-α-D-mannopyranosylbromid 
• 443915-98-8 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-1-C-(trimethylsilyl)-D-glycero-L-talo-oct-1-ynitol 
• 443916-30-1 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-talo-oct-1-ynitol 

Relevant academic research and scientific papers

Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling

A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.