110237-88-2Relevant academic research and scientific papers
Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2-Azidofuranoses, 2-Fluorofuranoses and Methyl Furanosyl Uronates
van der Vorm, Stefan,Hansen, Thomas,van Rijssel, Erwin R.,Dekkers, Rolf,Madern, Jerre M.,Overkleeft, Herman S.,Filippov, Dmitri V.,van der Marel, Gijsbert A.,Codée, Jeroen D. C.
, (2019/04/30)
The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these reactive intermediates is dictated by the conformation of these species. The nature and co
Synthesis of erythro and threo furanoid glycals from 1- and 2-phenylselenenyl-carbohydrate derivatives
Bravo, Fernando,Kassou, Mohamed,Diaz, Yolanda,Castillon, Sergio
, p. 83 - 97 (2007/10/03)
Differently protected erythro and threo furanoid glycals were synthesized by selenoxide elimination when phenyl 1-selenoglycosides were treated in oxidizing conditions (tBuOOH, Ti(OiPr)4, Et2iPrN). Th
Synthesis of erythro and threo furanoid glycals using 5-endo-trig selenoetherification as key step
Bravo,Kassou,Castillon
, p. 1187 - 1190 (2007/10/03)
Differently protected erythro and threo furanoid glycals were synthesised from 4-pentene-1,2,3-triol, through selenium induced 5-endo-trig cyclization and selenoxide elimination.
Synthesis of furanose glycals from furanose 1,2-diols and their cyclic thiocarbonate esters
Robles Diaz, Rafael,Rodriguez Melgarejo, Conception,Izquierdo Cubero, Isidoro,Plaza Lopez-Espinosa, Maria T.
, p. 375 - 380 (2007/10/03)
Two new methods for the synthesis of furanoid glycals are described. Both procedures were shown to be faster and cheaper that those previously reported. Protected 1,2-dihydroxypento- and hexo-furanose derivatives with the D-xylo, D-gluco and D-ribo, D-all
An efficient and highly stereoselective synthesis of nucleoside derivatives from furanoid 1,2-diols
Robles, Rafael,Rodriguez, Concepcion,Izquierdo, Isidoro,Plaza, Maria T.,Mota, Antonio
, p. 2959 - 2965 (2007/10/03)
Reaction between suitably protected furanoid glycals 1b-4b, readily obtained from furanoid 1,2-diols (1a-4a), and different silylated pyrimidine bases, gave the corresponding 3',5'- and 3',5',6'-O-protected 2'-deoxy-2'-iodo-β-D-xylo-pentofuranosyl 5-10 and β-D-gluco-hexofuranosyl 11 nucleosides, respectively. Compound 5 has been transformed into its 2'-deoxy 12 and 2',3'-anhydro 14 derivatives. The high stereoselectivity of the reaction is discussed.
Efficient Procedure for the Synthesis of Erythro and Threo Furanoid Glycals from 2-Deoxyribose
Kasson, Mohamed,Castillon, Sergio
, p. 5513 - 5516 (2007/10/02)
Differently protected erythro and threo furanoid glycals have been synthesised starting from 2-deoxyribose, via selenoxide elimination as the key step.
SELENIUM-CONTROLLED STEREOSELECTIVE SYNTHESIS OF 2'-DEOXYNUCLEOSIDES FROM GLYCALS. A FORMAL SYNTHESIS OF AZT
El-Laghdach, Anas,Diaz, Yolanda,Castillon, Sergio
, p. 2821 - 2822 (2007/10/02)
2'-Deoxynucleosides have been stereoselectively synthesized starting from glycals, using phenylselenyl reagents.Key Words: 2'-Deoxynucleosides, stereoselective glycosylation, glycals.
The Synthesis and Reactivity of Cyclic Thiocarbonates Derived from Some Carbohydrate 1,2-Diols
Patroni, Joseph J.,Stick, Robert V.,Tilbrook, D. Matthew G.,Skelton, Brian W.,White, Allan H.
, p. 2127 - 2141 (2007/10/02)
The attempted synthesis of several carbohydrate 1,2-diols is reported, together with the transformation of two of these diols into cyclic thiocarbonates, namely 4,6-O-benzylidene-3-O-methyl-1,2-O-thiocarbonyl-α-D-glucose and 3,4-O-isopropylidene-1,2-O-thiocarbonyl-β-D-arabinose.The treatment of these thiocarbonates, and a furanose 1,2-thiocarbonate previously prepared by Mukaiyama, with methyl halides and with tributyltin hydride is discussed.A single-crystal X-ray diffraction study of 3,4-O-isopropylidene-1,2-O)-thiocarbonyl-β-D-arabinose is recorded.
