A convenient synthesis of 2′-O-acetal-N2-acyl derivatives of riboguanosine (original) (raw)

Recueil des Travaux Chimiques des Pays-Bas, 2010

Abstract

ABSTRACT The partially protected and crystalline 2′-O-levulinoyl-3′5′-O-(tetraisopropyldisiloxane-1,3-diyl)guanosine derivative (4) serves as a key intermediate for the synthesis of 2′-O-acetal-N2-acylriboguanosines 1c. Acylation of 4 with diphenylacetic anhydride gave, after hydrazinolysis of the levulinoyl group, the N2-acyl derivative 6 in high yield. Acylation of 4 with benzoyl or biphenyl-4-carbonyl chloride afforded the corresponding N2-acyl derivatives in lower yields. Acetalization of derivatives 6 with 4-methoxy-5,6-dihydro-2H-pyran, followed by the removal of the 1,1,3,3-tetraisopropyldisiloxane-1,3-diyl (TIPS) group, gave the corresponding 2′-O-acetal-N2-acylriboguanosines 1c.

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