450409-37-7

Upstream product

• 450409-36-6 methyl (methyl 7-O-benzyl-4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-oct-2-ulopyranosid)-onate 
• 81927-55-1 O-benzyl 2,2,2-trichloroacetimidate 
• 93215-23-7 methyl (methyl 4,5-O-carbonyl-3-deoxy-8-O-triphenylmethyl-α-D-manno-2-octulopyranosid)onate 

Downstream Products

• 450409-38-8 methyl (methyl 2-O-benzyl-4,5-O-carbonyl-6-deoxy-α-D-manno-oct-7-ulo-4,7-pyranosid)-onate 

Relevant academic research and scientific papers

Synthesis of C-8 deuterated glycosides of 3-deoxy-D-manno-oct-2-ulosonic acid (Kdo) related to chlamydial lipopolysaccharides

Methyl glycosides of Kdo and a (2→8)-linked Kdo disaccharide were prepared which contain a deuterium label at C-8 of the reducing unit. The label was introduced in fair diastereoselectivity upon reduction of an aldehyde group using a chiral borane complex derived from N-benzyloxycarbonyl-(S)-proline which produced the 8-(S)-deuterated derivative as the major isomer. Further coupling with a Kdo bromide gave the α-(2→8)-linked disaccharide in good yield. The deprotected disaccharide serves as a model for NMR spectroscopic studies on the side chain conformation of a carbohydrate epitope from the bacterial pathogen Chlamydia.