260551-08-4

Upstream product

• 768385-13-3 (2-acetamido-3,4,6-tri-O-benzyl-1,2-dideoxy-α-D-glucopyranosyl) cyanide 
• 180778-36-3 3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene 
• 121123-45-3 3,4,6-tri-O-benzyl-2-acetamido-2-deoxyamino-α-D-glucopyranose 
• 537031-63-3 (E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene 
• 262286-48-6 3-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-1-propene 
• 214193-76-7 1-(2'-acetamido-2'-deoxy-α-D-glucopyranosyl)-2-propene 
• 652993-93-6 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose 

Downstream Products

• 260551-09-5 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptonic acid methyl ester 
• 768385-14-4 S-(4-methylphenyl) 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-hepto-pyranosonothioate 
• 652993-95-8 (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-ido-heptitol-1-yl) dibenzyl phosphate 
• 768385-15-5 (3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-erythro-L-ido/L-gulo-heptitol-1-C-yl) dibenzyl phosphonate 
• 260551-11-9 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-1-hydroxy-D-glycero-D-ido-heptitol 

Relevant academic research and scientific papers

C-glycosidic UDP-GlcNAc analogues as inhibitors of UDP-GlcNAc 2-epimerase

The first step in the biosynthesis of neuraminic acid, the "epimerisation" of UDP-GlcNAc to ManNAc, is catalyzed by UDP-GlcNAc 2-epimerase. In this paper we report the synthesis of the C-glycosidic UDP-GlcNAc analogues 1-5 as substrate-based inhibitors of this enzyme. The focus is on the optimal distance and geometry of the connection between the sugar and the UDP-moiety, which are both important for recognition by UDP-GlcNAc 2-epimerase. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

Synthesis of α- and β-C-glycosides of N-acetylglucosamine

As part of efforts to make available new classes of bioactive C-glycoconjugates, D-glucosamine has been effectively converted into a series of 2-deoxy-2-amino-C-glycosides. This versatile approach is keyed by a remarkably effective metal catalyzed olefin isomerization of the isomeric C-allyl amino sugars which, in turn, are readily available via radical allylation of D-glucosamine.

Synthesis of Novel Donor Mimetics of UDP-Gal, UDP-GlcNAc, and UDP-GalNAc as Potential Transferase Inhibitors

For the enzymatic transfer of galactose, N-acetylglucosamine, and N-acetylgalactosamine, UDP-Gal (1), UDP-GlcNAc (2), and UDP-GalNAc (3) are employed, and UDP serves as a feedback inhibitor. In this paper the synthesis of the novel UDP-sugar analogues 4, 5, and 6 as potential transferase inhibitors is described. Compounds 4-6 feature C-glycosidic hydroxymethylene linkages between the sugar and nucleoside moieties in contrast to the anomeric oxygens in the natural derivatives 1-3.