256949-49-2

Upstream product

• 65-71-4 thymin 
• 256949-47-0 (3R,5S)-5-acetyloxy-2-(5'-O-tert-butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonylisoxazolidine 
• 256949-46-9 (3R,5R)-5-acetyloxy-2-(5'-O-tert-butyldiphenylsilyl-2',3'-O-isopropylidene-β-D-ribofuranosyl)-3-ethoxycarbonylisoxazolidine 
• 924-44-7 glyoxylic acid ethyl ester 
• 20245-84-5 1-vinylthymine 

Downstream Products

• 627486-12-8 1-[(3R,5S)-2-(5-O-tert-butyldiphenylsilyl-2,3-O-isopropylidene-β-D-ribofuranosyl)-3-hydroxymethyl-1,2-isoxazolidin-5-yl]-5-methyl-1H-pyrimidine-2,4-dione 

Relevant academic research and scientific papers

Diastereo- and enantioselective synthesis of N,O-nucleosides

The diastereo- and enantioselective synthesis of α- and β-3′-hydroxymethyl-N,O-nucleosides is described, based on the 1,3-dipolar cycloaddition of a N-glycosyl nitrone. Two approaches have been evaluated: the one-step procedure, which uses vinyl nucleobases, showed a better stereoselectivity towards β-nucleosides.

Homochiral α-D- and β-D-isoxazolidinylthymidines via 1,3-dipolar cycloaddition

The introduction of chiral auxiliaries at the C- or N-atom in starting nitrones has been investigated as a stereoselective synthetic route to heterocyclic nucleoside analogues. The carbohydrate auxiliary at nitrogen atom gave the best results, thus allowi