503544-29-4

Upstream product

• 613-90-1 benzoyl cyanide 
• 503544-21-6 7,8,9-tri-O-acetyl-2,6-anhydro-4,5-O-carbonylidene-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-talo-nonitol 

Downstream Products

• 503544-31-8 2,6-anhydro-5-azido-4,7,8,9-tetra-O-benzoyl-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-manno-nonitol 
• 503544-32-9 4,7,8,9-tetra-O-acetyl-2,6-anhydro-5-azido-1,3-dideoxy-2-methyl-1-phenylseleno-D-erythro-L-manno-nonitol 
• 503544-30-7 2,6-anhydro-4,7,8,9-tetra-O-benzoyl-1,3-dideoxy-2-methyl-5-O-trifluoromethanesulfonyl-1-phenylseleno-D-erythro-L-talo-nonitol 

Relevant academic research and scientific papers

Synthesis of C-glycosyl compounds of N-acetylneuraminic acid from D-gluconolactone

A general strategy towards the synthesis of C-glycosyl compounds of N-acetylneuraminic acid (Neu5Ac) has been developed and successfully applied to the synthesis of C-methyl and C-phenyl derivatives. The key strategic elements are (i) chain extension of a D-gluconolactone derivative as C6-precursor with an allyl Grignard reagent as C3-precursor having in 2 position the C-linked aglycon moiety, (ii) stereoselective C-4/C-5 erythro-diol formation, (iii) 6-exo-trig selective heterocyclization, and (iv) instalment of the 5-acetylamino and C-1 carboxylate functionalities. The efficiency and potential versatility of this approach was exemplified in the synthesis of C-methyl derivative 1 as target molecule.