84366-59-6Relevant articles and documents
Synthesis, Reactivity, and Stereoselectivity of 4-Thiofuranosides
Madern, Jerre M.,Hansen, Thomas,Van Rijssel, Erwin R.,Kistemaker, Hans A.V.,Van Der Vorm, Stefan,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.,Codée, Jeroen D.C.
, p. 1218 - 1227 (2019/01/25)
Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans because the thiosugar glycosydic linkage is supposed to be stabilized toward chemical and enzymatic hydrolysis. We have performed an in-depth investigation into the stability and reactivity of furanosyl thiacarbenium ions, by assessing all four diastereoisomeric thiofuranosides experimentally and computationally. We show that all furanosyl thiacarbenium ions react in a 1,2-cis-selective manner with triethylsilane, reminiscent of their oxo counterparts. The computed conformational space occupied by the thiacarbenium ions is strikingly similar to that of the corresponding furanosyl oxycarbenium ions, indicating that the stereoelectronic substituent effects governing the stability of furanosyl oxocarbenium ions and thiacarbenium ions are very similar. While the thio-ribo-furanose appears to be less reactive than its oxo counterpart, the thio-ara-, lyxo-, and xylo-furanosides appear to be more reactive than their oxygen equivalents. These differences are accounted for using the conformational preference of the donors and the carbocation intermediates. The lower reactivity of the thio-ribo furanosides in (Lewis) acid-mediated reactions and the similarity of the thia- and oxocarbenium ions make thio-ribo-furanosides excellent stabilized analogues of the naturally occurring ribo-furanose sugars.
Efficient stereoselective synthesis of oligosaccharides of Streptococcus pneumoniae serotypes 6A and 6B containing multiple 1,2-cis glycosidic linkages
Parameswar, Archana R.,Pornsuriyasak, Papapida,Lubanowski, Nicole A.,Demchenko, Alexei V.
, p. 10083 - 10091 (2008/02/13)
The synthesis of the repeating units of pneumococcal polysaccharide serotypes 6A and 6B and derivatives thereof is described. Application of S-benzoxazolyl and S-thiazolinyl glycosides allowed rapid oligosaccharide assembly and provided complete stereosel
The stereoselective synthesis of 4'-β-thioribonucleosides via the pummerer reaction
Naka, Takashi,Minakawa, Noriaki,Abe, Hiroshi,Kaga, Daisuke,Matsuda, Akira
, p. 7233 - 7243 (2007/10/03)
An efficient stereoselective synthesis of 4'-β-thioribonucleosides 14, 15, 27, and 30 using the Pummerer reaction as the key step is described. The Pummerer reaction of 1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopro pyldisiloxane-1,3-di
