78119-26-3Relevant academic research and scientific papers
Stereoselectivity in the Lewis acid mediated reduction of ketofuranoses
Van Rijssel, Erwin R.,Van Delft, Pieter,Van Marle, Daan V.,Bijvoets, Stefan M.,Lodder, Gerrit,Overkleeft, Herman S.,Van Der Marel, Gijsbert A.,Filippov, Dmitri V.,Codée, Jeroen D.C.
, p. 4553 - 4565 (2015/05/13)
The Lewis acid mediated reduction of ribose-, arabinose-, xylose-, and lyxose-derived methyl and phenyl ketofuranoses with triethylsilane as nucleophile was found to proceed with good to excellent stereoselectivity to provide the 1,2-cis addition products
A Synthesis of Pseudouridine
Brown, Daniel M.,Ogden, Richard C.
, p. 723 - 725 (2007/10/02)
2,3,5-Tri-O-benzylribose and 2,4-di-t-butoxy-5-lithiopyrimidine (from the 5-bromo-compound and butyllithium) in THF at -78 deg C give 5-(2,3,5-tri-O-benzyl-D-altro-pentahydroxypentyl)-2,4-di-t-butoxypyrimidine and its D-allo-epimer (ratio 5:2), which cyclise sterospecifically in ethanolic hydrochloric acid to 5-(2,3,5-tri-O-benzyl-β-D-ribofuranosyl)uracil and its α-anomer.Debenzylation by boron trichloride gives 5-β-D-ribofuranosyluracil, pseudouridine, and its α-anomer. 2,3,5-Tri-O-methylribose reacts analogously. 2,3-O-Isopropylideneribose and its 5-O-trityl derivative give no polyol, but instead 2,4-di-t-butoxy-5-(2-hydroxyisopropyl)pyrimidine.
