144002-22-2Relevant academic research and scientific papers
Convenient chemical synthesis of CMP-N-acetylneuraminate (CMP-Neu-5-Ac)
Martin, Thomas J.,Schmidt, Richard R.
, p. 1765 - 1768 (1993)
Reaction of sialyl phosphites 1 and 2 with dibenzyl phosphate and phenyl phosphate furnished without addition of a catalyst directly the corresponding sialyl phosphates 3 and 4, respectively, in good yields. Similarly, reaction of 1 with acetylated CMP 5 afforded exclusively β-configurated acetylated CMP-Neu-5-Ac (6); which was readily transformed into natural sialyl donor CMP-Neu-5-Ac (7).
Conversion of N-acetylneuraminic acid glycosyl chloride into dibenzyl glycosyl phosphate: O-glycosylation in the absence of a promoter
Shpirt,Kononov,Torgov,Shibaev
, p. 717 - 719 (2004)
Readily accessible N-acetylneuraminic acid (Neu5Ac) glycosyl chloride, which was regarded to be a poor glycosyl donor, was shown to react with dibenzyl phosphoric acid salts in the absence of glycosylation promoters to give the corresponding β-Neu5Ac dibenzyl glycosyl phosphate in high yield.
N,N-Diacetylsialyl chloride-a novel readily accessible sialyl donor in reactions with neutral and charged nucleophiles in the absence of a promoter
Orlova, Anna V.,Shpirt, Anna M.,Kulikova, Nadezhda Y.,Kononov, Leonid O.
scheme or table, p. 721 - 730 (2010/06/14)
N,N-Diacetylneuraminic acid glycosyl chloride was prepared for the first time and made to react with various nucleophiles to give the corresponding α-glycosyl phosphate, β-glycosyl dibenzyl phosphate, α-glycosyl azide, α-phenyl thioglycoside and α-glycosyl xanthate in 65-82% yields and high stereoselectivity while its reactions with simple alcohols were not stereoselective. The new sialyl donor made possible the first stereoselective synthesis of sialic acid glycosyl phosphate with α-configuration and highly efficient synthesis of β-configured sialic acid glycosyl dibenzyl phosphate.
Synthesis and use of glycosyl phosphites: An effective route to glycosyl phosphates, sugar nucleotides, and glycosides
Sim, Mui Mui,Kondo, Hirosato,Wong, Chi-Huey
, p. 2260 - 2267 (2007/10/02)
An efficient and convenient synthetic route to glycosyl phosphites and phosphates has been developed that uses dibenzyl N,N-diethylphosphoramidite as a phosphitylating reagent. Glycosyl phosphites and phosphates of 2-acetamido-2-deoxy-D-galactose (GalNAc) (29), 2-acetamido-2-deoxy-D-glucose (GlcNAc) (30), D-galactose (Gal) (31), D-glucose (Glc) (32), D-mannose (Man) (33), L-rhamnose (Rha) (34), L-fucose (Fuc) (35), and N-acetylneuraminic acid (NeuAc) (41) were prepared by this procedure. Compounds 29 and 30 were obtained as α anomers exclusively, whereas compounds 31, 32, and 41 were obtained as β anomers, and compounds 33 and 34, as α anomers, predominately. The phosphates are useful for the synthesis of sugar nucleotides, and the phosphites are effective glycosylation reagents.
