A Reverse Strategy for synthesis of nucleosides based on n-pentenyl orthoester donors
Bert Fraser-Reid1, Parimala Ganney, Changalvala V S Ramamurty
1Natural Products and Glycotechnology Research Institute Inc., 595 F Weathersfield Road, Pittsboro, NC 27312, USA. dglucose@aol.com
Abstract:
Strategically derivatized NPOE glycosyl donors, are able to efficiently glycosylate silylated nucleobases under mild conditions, even as low as -78 °C if necessary. Ensuring trans-1,2 glycosylation, thus permitting, unlike classical procedures, a Reverse Strategy for the synthesis of ribonucleosides, where glycosylation occurs late, rather than early, and convergency is optimized.
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