102650-60-2Relevant academic research and scientific papers
REACTIONS OF VICINAL DITRIFLATES WITH BENZOATE AND NITRITE ANIONS
Binkley, Roger W.
, p. 111 - 124 (2007/10/02)
The four possible methyl 2,6-dideoxy-β-D-hexopyranosides were converted into the corresponding vicinal ditriflates 1-4 and these compounds (1-4) were reacted with tetrabutylammonium benzoate and with tetrabutylammonium nitrite.In most cases two SN/s
Inversion of Configuration in 2,6-Dideoxy Sugars. Triflate Displacement by Benzoate and Nitrite Anions
Binkley, Roger W.
, p. 3892 - 3896 (2007/10/02)
Interconversion among 2,6-dideoxy sugars at room temperature has been accomplished in high yield.The eight possible methyl 3- and 4-O-benzoyl-2,6-dideoxy-β-D-hexopyranosides 1-8 have been interconverted using their corresponding triflates as intermediates.Triflates derived from compounds 1, 2, 7, and 8 undergo internal displacement by the neighboring benzoyl group, inverting configuration at the triflyloxy-bearing carbon atom.Triflates of compounds 3-6 do not experience internal reaction; however, configuration was inverted in these compounds at room temperature byreaction with tetrabutylammonium nitrite.To illustrate the value of these reactions in oligosaccharide synthesis, configuration was inverted in three disaccharides composed of 2,6-dideoxy sugar residues.
A Reactive Intermediate Formed by Triflate Rearrangement. A New Displacement Reaction for Carbohydrate Synthesis
Binkley, Roger W.,Sivik, Matthew R.
, p. 2619 - 2621 (2007/10/02)
Treatment of methyl 4-O-benzoyl-2,6-dideoxy-β-D-arabino-hexopyranoside (3) with triflic anhydride results in formation of a rearranged triflate, a new and promising type of reactive intermediate for syntheses involving carbohydrates.
