161016-65-5

Upstream product

• 110-91-8 morpholine 
• 146763-12-4 2',3'-di-O-mesyl-5'-O-trityl-(1-β-D-lyxofuranosyl)uracil 
• 76-83-5 trityl chloride 
• 4348-61-2 uridine 
• 176696-21-2 2'-O-pivaloyl-3'-O-mesyl-5'-O-trityluridine 
• 6554-10-5 5'-O-trityluridine 

Downstream Products

• 38359-55-6 5'-O-benzoyl-3'-deoxy-2'-keto-β-uridine 

Relevant academic research and scientific papers

One-pot deoxygenative conversion of a ribonucleoside to enaminonucleosides involving 1,2-hydride shift rearrangement

5'-O-Trityl-3'-O-mesyluridine on reaction with secondary amines produced 1-(2,3-dideoxy- 2-N-dialkylamino-5-O-trityl- D-glycero--pent-2-enofuranosyl) uracil involving 1,2-hydride shift. The reaction proceeded through the formation of 2'-ketouridine in situ which was evident from the formation of both the α- and β-anomers of the enaminonucleosides.

Reactions of 2′,3′-Di-O-mesyl-lyxo-uridine with secondary amines: First report on the one-pot conversion of mesylated nucleosides to enaminonucleosides and the crystal structure of α-enamine

2′,3′-Di-O-mesyl-5′-O-trityl-lyxo-uridine 1 reacted with secondary amines to produce enaminonucleosides 2a-d and 3a-d. Intermediacy of 2′-ketouridine was essential for the anomerisation and enamine formation to take place. The structure of the β-enamine was established unambiguously by analysing the hydrolysed product and that of α-enamine was proved with the help of crystal structure analysis.