3′-Deoxy-3′-(vinylsulphonyl)thymidine — a new reactive analogue of AZT: its synthesis and reactivities towards various nucleophiles

On the Bis‐Heteronucleophilic Michael Addition to Divinyl Sulfone: A New Efficient Access to Macrocycles by Marie‐Laure Teyssot, Martine Fayolle, Christian Philouze and Claude Dupuy

“…1 was also on “The Michael addition of bis(nitrogen or sulfur) nucleophiles, e.g. diaza‐18‐crown‐6, to divinyl sulfone ...”,3 we would like to point out that we reported in an earlier paper4 the attachment of a macrocycle, 1,4,10,13‐tetraoxa‐7,16‐diazacyclooctadecane, to another organic moiety, namely a nucleoside, through an ethylenesulfone linker as shown below.…”

“…The authors also overlooked the existence of, perhaps, the only paper4 prior to their paper1 that dealt with the concept of attaching a macrocycle with another organic molecule by a Michael addition reaction to a vinyl sulfone functionality. A computer‐based literature search using partial structure of the ethylenesulfone‐linked macrocycle revealed two publications in this area − one is their paper in the Eur.…”

Sugar-Modified Uridine Bisvinyl Sulfone: Synthesis of a Bifunctionalized Nucleoside Michael Acceptor and Its Use in Stereoselective Tandem Cyclization

“…Attempts have been made in the recent past to synthesize chemically reactive analogues of AZT that may form a covalent bond to viral reverse transcriptase. Since vinyl sulfones, highly reactive Michael acceptors, reportedly 1,2 show their activities by forming covalent bonds with biological nucleophiles, we decided to incorporate vinyl sulfone functionality at the carbohydrate moieties of nucleosides. After studying 5 the reactivities of 3‘-deoxy-3‘- S -vinylsulfonylthymidine 16 with various nucleophiles, we envisaged that modified nucleosides equipped with a bisvinyl sulfone functional group would also have the potential to form covalent linkages with biological nucleophiles since bisvinyl sulfone has also been reported 1 to be an efficient enzyme inhibitor.…”

A Glycosylation Driven Strategy for the Synthesis of Anomerically Pure Vinyl Sulfone-modified Pent-2-enofuranoses and Hex-2-enopyranoses

“…During the course of our studies on the synthesis and properties of carbohydrate modified monovinyl sulfone 13 and bisvinyl sulfone 14 substituted nucleosides, we envisaged that due to the high reactivities of vinyl sulfones towards various nucleophiles, vinyl sulfone-modified carbohydrates could be utilized to generate a wide variety of modified monosaccharides.…”