183073-97-4Relevant academic research and scientific papers
Sulfurization of dinucleoside phosphite triesters with chiral disulfides
Mukhlall, Joshua A.,Hersh, William H.
experimental part, p. 706 - 725 (2012/01/03)
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. Copyright Taylor and Francis Group, LLC.
