70209-12-0Relevant academic research and scientific papers
Synthesis of tetrazole-fused glycosides by a tandem fragmentation- cyclization reaction
Paz, Nieves R.,Santana, Andrés G.,Francisco, Cosme G.,Suárez, Ernesto,González, Concepción C.
supporting information; experimental part, p. 3388 - 3391 (2012/08/28)
The fragmentation of anomeric alkoxyl radicals (ARF) and the subsequent intramolecular cyclization promoted by hypervalent iodine reagents provide an excellent method for the synthesis of tetrazolo-sugars. This new reaction offers additional advantages for the synthesis of these compounds, including the ready availability of the starting materials, experimental simplicity, mild conditions, and good yields.
Alkoxyl Migration in Displacement of a 5-Trifluoromethanesulfonyloxy Group from Ribofuranosides
Iyer, Vaidyanathan K.,Horwitz, Jerome P.
, p. 644 - 649 (2007/10/02)
Methyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside (2) reacts at room temperature with primary aralkanols such as benzyl alcohol and the steroid alcohols 3a,b in dichloromethane and in the presence of sodium sulfate to give the corresponding aralkyl 2,3-O-isopropylidene-5-O-methyl-β-D-ribofuranosides 5a,b and 11 in 40-45percent yields.Migration of the methoxyl group from C-1 to C-5, via a tricyclic oxonium ion (7a), is suggested as the basis of formation of the new β-glycoside.Anchimeric assistance by a benzyloxy group in the displacement of the sulfonate is observed in the reaction of benzyl 2,3-O-isopropylidene-5-O-triflyl-β-D-ribofuranoside (14) with methanol, which affords methyl 5-O-benzyl-2,3-O-isopropylidene-β-D-ribofuranoside (15) in 40percent yield on treatment with Na2SO4 in CH2Cl2.The elements of anomeric control in these facile transformations remain to be elaborated.
