756485-54-8Relevant academic research and scientific papers
Synthesis of thiosaccharides employing the Pummerer rearrangement of tetrahydrothiopyran oxides
Fujita, Junji,Matsuda, Hiroko,Yamamoto, Kazunori,Morii, Yasuharu,Hashimoto, Masaru,Okuno, Toshikatsu,Hashimoto, Kimiko
, p. 6829 - 6851 (2004)
The Pummerer rearrangement of 1-deoxy-5-thioglucopyranose derivatives carrying acetonides at the C3,4-positions proceeded regioselectively at the C1 position by treating with TFAA in the presence of pyridine. Studies employing deuterium-labelled derivatives revealed that the reaction was induced by E2 1,2-elimination of trifluoroacetic acid of the trifluoroacetoxy sulfonium intermediate. This methodology was applied to the synthesis of an isomaltotriose derivative consisting of 5-thioglucopyranoside units.
