175013-53-3

Upstream product

• 622-33-3 N-benzyloxyamine 
• 3736-77-4 2,2'-Anhydrouridine 
• 175013-51-1 3'-O-(benzyloxyamino)carbonyl-5'-O-tert-butyldiphenylsilyl-2,2'-anhydrouridine 
• 185022-13-3 Imidazole-1-carboxylic acid (2R,3R,3aS,9aR)-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-oxo-2,3,3a,9a-tetrahydro-6H-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-3-yl ester 
• 175013-46-4 (2R,3R,3aS)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}3-hydroxy-2,3,3a,9a-tetrahydro-6H-furo[2’,3’:4,5]oxazole[3,2a]-pyrimidin-6-one 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 176685-71-5 1-[(2R,3R,4S,5R)-3-Benzyloxyamino-5-(tert-butyl-diphenyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 175013-49-7 5'-O-(tert-butyldiphenylsilyl)-2'-N,3'-O-carbonyl-2'-deoxy-2'-(hydroxylamino)uridine 
• 219618-70-9 5'-O-(tert-butyldiphenylsilyl)-2'-amino>-2'-deoxyuridine 
• 219618-65-2 5'-O-(tert-butyldiphenylsilyl)-3'-O-(trimethylsilyl)-2'-deoxy-2'--N-methylamino>cytidine 
• 219618-63-0 5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2-(N-hydroxy-N-methylamino)uridine 
• 214055-31-9 3'-O-(tert-butyldimethylsilyl)-5'-O-(tert-butyldiphenylsilyl)-2'-deoxy-2'-<(2-tetrahydrofuranyl)oxyamino>uridine 

Relevant academic research and scientific papers

Novel nucleosides via intramolecular functionalization of 2,2'-anhydrouridine derivatives

The generation of novel ribonucleoside analogues derived from 2,2'-anhydrouridines by a 3'-hydroxyl directed intramolecular nucleophilic substitution of the 2'-position is described. The methodology allows for the efficient, regio- and stereoselective elaboration of the 2'-position, often under exceptionally mild reaction conditions.

2'-Deoxy-2'-alkoxyaminouridines: Novel 2'-substituted uridines prepared by intramolecular nucleophilic ring opening of 2,2'-O-anhydrouridines

Natural and unnatural modified nucleosides and nucleotides play important roles in biology, medicine, and as biomedical research tools. Reported herein is an application of synthetic methodology developed for the stereo- and regiospecific introduction of structural modifications at the 2'-position of uridine nucleosides. A novel class of modified nucleosides, 2'-alkoxylamino-2'-deoxy uridines, are prepared by intramolecular nucleophilic addition of a 3'-tethered alkoxycarbamate nucleophile to the 2'-position with concomitant opening of a 2,2'-anhydrouridine.