Deazapurine analogues that possess pyrrolopyrimidines as the nucleobase are common bioisosteres of adenosine. In the course of our research, we desired a flexible and reliable method to form the glycosyl linkage between novel pyrrolopyrimidines and a ribose core that did not require numerous protecting group operations.  Traditional carbohydrate chemistry uses fully protected sugars and requires either displacement of an anomeric halide with a deprotonated pyrrolopyrimide or Vorbruggen type chemistry using in situ silylated pyrrolopyrimidine and Lewis acid activation. We were intrigued by the recent published work from Mahrwald and Hocek who reported direct glycosylation of purine and pyrimidine nucleosides with unprotected or 5-O-monoprotected D-ribose using Mitsunobu conditions.  However, 3-iodo-5-chloro pyrrolopyrimidine was the only deazapurine example shown in the publication.  Herein, we show that under modified conditions, the Mitsunobu glycosylation conditions can be applied to novel pyrrolopyrimidine nucleobases.  Utilizing 5-O-monoprotected D-ribose, we demonstrate easy access to novel deazapurine analogues with minimal protecting group manipulations. <br/>

Development and utilization of Mitsunobu glycosylation conditions to install pyrrolopyrimidine nucleobases onto a ribose core

254th National Meeting (2017)

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