01705nas a2200229   4500008004100000022001400041245010000055210006900155260009900224300001400323490000800337520079800345653001101143653003001154653002101184653002801205653003901233100002601272700003001298700002001328856012701348       2008                        eng d  a0008-621500aStudies on the synthesis and unusual behavior of vinyl sulfone-modified hexenopyranosylthymines0 aStudies on the synthesis and unusual behavior of vinyl sulfonemo  aTHE BOULEVARD, LANGFORD LANE, KIDLINGTON, OXFORD OX5 1GB, OXON, ENGLANDbELSEVIER SCI LTDcMAY  a1163-11700 v3433 a<p>Although vinyl sulfone-modified- (VSM) pent-2-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycoside 4 are easily synthesized from the corresponding mesylated sulfones le and 3c, respectively, via an oxidation-mesylation-elimination route, the 3'-C-sulfonyl-hex-2'-enopyranosylthymine 11 is not obtained from 10 and a glycal derivative 12 is formed instead. On the other hand, 3-C-sulfonyl-hex-3'-enopyranosylthymine 20 is easily synthesized from the mesylated sulfone 19. Again unlike the reaction patterns of VSM-pent-T-enofuranosyl nucleosides 2 and hex-2-enopyranosyl glycosides 4 as Michael acceptors, the reactions of nucleophiles with 3'-C-sulfonyl-hex-3'-enopyranosylthymine 20 yielded a rearranged product 21 instead of Michael adducts. (c) 2008 Published by Elsevier Ltd.</p>10aglycal10ahexopyranosyl nucleosides10aMichael addition10aunsaturated nucleosides10avinyl sulfone-modified nucleosides1 aDeshpande, Sachin, G.1 aSuresh, Cheravakkattu, G.1 aPathak, Tanmaya  uhttps://library.ncl.res.in/content/studies-synthesis-and-unusual-behavior-vinyl-sulfone-modified-hexenopyranosylthymines-0