Carbohydrate Research p. 77 - 90 (1989)
Update date:2022-08-04
Topics: Chemical shifts NMR Triethylamine Silica gel Dichloromethane Coupling constants CDCl3 Analytical calc C, H, O, Se, Si Methyl 1,6-di-0-(tert-butyldinzPthylsilyl)-3-O_-selerzo-P-I,lfructoSurenosine Methanesulfonyl chloride NaHCO3
Martin, Olivier R.
Rafka, Robert J.
Szarek, Walter A.
4-Seleno-D-fructose derivatives were prepared by opening of the epoxide ring of methyl 2,3-anhydro-α- and β-D-tagatofuranosides with phenyl selenide ion.The resulting β-hydoxyselenide system or the corresponding methanesulfonate could not be induced to undergo elimination, thus providing the first examples of stable β-methylsulfonyloxyselenides.Oxidation of methyl 1,6-di-O-(tert-butyldimethylsilyl)-3-O-methylsulfonyl-4-Se-phenyl-4-seleno-α-D-fructofuranoside to the corresponding selenoxide, followed by thermally induced syn-elimination of benzeneselenenic acid, provides a convenient route to the novel unsaturated hexulofuranoside, methyl 1,6-di-O-(tert-butyldimethylsilyl)-4-deoxy-β-L-glycero-hex-4-enulofuranoside, which was readily converted into methyl 4-deoxy-α-D-threo-hexulofuranoside.
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Doi:10.1021/ja078081n
(2008)Doi:10.1248/cpb.41.611
(1993)Doi:10.1021/ol702965r
(2008)Doi:10.1016/j.tet.2007.11.063
(2008)Doi:10.1021/ja01480a027
(1961)Doi:10.1002/jhet.728
(2013)