Synthesis and stability studies of 2',3',5'-tri-O-acetyl-2-amino(-N6-cyclopentyl)-1-deazaadenosines.
In this article, we report on the synthesis of 2',3',5'-tri-O-acetyl-2-amino-1-deazaadenosine and of 2',3',5'-tri-O-acetyl-2-amino-N(6)-cyclopentyl-1-deazaadenosine, which are very versatile intermediates for the preparation of 2-substituted 1-deazaadenosine derivatives. The two synthesized compounds showed to be quite unstable, with the N(6)-substituted derivatives being less stable than the N(6)-unsubstituted counterpart, according to the calculated HOMO-LUMO energy gap. Stability studies were performed through HPLC-MS analysis.
Vittori
Sauro
S
Dipartimento di Scienze Chimiche, Università di Camerino, I-62032 Camerino, MC, Italy. sauro.vittori@unicam.it
Mishra
Ram Chandra
RC
Dal Ben
Diego
D
Kachare
Dhuldeo
D
Lambertucci
Catia
C
Volpini
Rosaria
R
Cristalli
Gloria
G
D000241:Adenosine / Q000031:analogs & derivatives*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C527078:2'-deoxy-2'-C-(thymine-1-ylmethyl)uridine; D000241:Adenosine; D014529:Uridine