Joshua A. Mukhlall, W. Hersh
Sep 1, 2011
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0
Influential Citations
8
Citations
Journal
Nucleosides, Nucleotides & Nucleic Acids
Abstract
Sixteen chiral analogues of phenylacetyl disulfide (PADS) and 5-methyl-3H-1,2,4-dithiazol-3-one (MEDITH) were used to sulfurize five dithymidine phosphite triesters, each incorporating a β-cyanoethoxy or siloxy group. Each mixture of SP:RP phosphite triester diastereomers was combined with approximately one fourth of an equivalent of each of the sulfurizing reagents, and the RPS:SPS diastereomer ratios of the resulting phosphite sulfides or phosphorothioates were determined by reverse-phase HPLC. Diastereoselectivities and corresponding diastereomeric excess (de) values were calculated by correcting for the starting triester diastereomer ratios. The highest de values for RPS and SPS phosphorothioates were 14.7% and 7.9%, respectively, both using MEDITH analogues.