Organocatalytic Conversion of Nucleosides to Furanoid Glycals
Edna Mao1, Cheol K Chung1, Yining Ji1
1Department of Process Research and Development, Merck & Co., Inc., Rahway, New Jersey 07065, United States.
Abstract:
A class of organocatalysts that are highly active for the conversion of 2'-deoxynucleosides to furanoid glycals have been discovered. These phosphorimides, (Ph2PS)2NH and (Ph2PSe)2NH, were shown to effectively mediate persilylation of 2'-deoxynucleosides allowing the elimination of the nucleobase giving the corresponding glycal. These mild conditions were demonstrated in the syntheses of glycals with various substitution patterns while minimizing the formation of undesired byproducts and expanding the scope of this methodology.
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