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.
✍ Scribed by Kandasamy Sakthivel; Tanmaya Pathak; Cheravakkattu G Suresh
- Publisher
- Elsevier Science
- Year
- 1994
- Tongue
- French
- Weight
- 830 KB
- Volume
- 50
- Category
- Article
- ISSN
- 0040-4020
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✦ Synopsis
Abstmctz 2',3'-Di-0-mesyl-S'-O-trityl-lyxo-uridine 1 tracted with secondary amines to produce cnaminooucleosidcs t-d and 3a-d. Intermediacy of 2'-ketouridine was essential for the anomerisation and enamiue formation to take place. The structure of the gcnamine was established unambiguously by anal ysing the hydrolysed product and that of a-ennmine was proved witb the help of crystal structure analysis. AR attempts to get propet elemental amal yses of the crystals of compounds 3s-d failed. Similar problem was faced by other grotqxk Compounds 9n and 1Oa were rather unstable. Heating in solution or leaving in ~~ion(f~c~stalli~tion) caused the degradation of the compounds. Formation of 2,2'-anhydro-3'-deoxy3'-morpholinouridine through aziridinium intsrmediates was highly probable".