Sulfone cleavability

Figure 4.8 BSOCOES reacts with amine-containing molecules to create amide bond crosslinks. The internal sulfone group is cleavable under alkaline conditions.

A new radical allylation procedure has been applied to the synthesis of a 3 -C-allyl-2, 3 -dideoxypyrimidine nucleoside, and lactone 121, made by photochemical addition of isopropanol to the corresponding 2,3-ene, has been converted to the nucleoside 122. Branched-chain sulfonates 123 have been made from 3 -ketonucleosides, and the isobutyl group was found to be superior to other possibilities, it being cleavable by iodide ion to give the sulfonic acid, an analogue of a 3 -phosphate. An ingenious route to related phosphonates is outlined in... 

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