152420-91-2Relevant academic research and scientific papers
Recent advances in the synthesis of 2-deoxy-glycosides
Hou, Dianjie,Lowary, Todd L.
scheme or table, p. 1911 - 1940 (2010/03/01)
Glycosides of 2-deoxy-sugars, monosaccharides in which the hydroxyl group at C-2 is replaced with a hydrogen atom, occur widely in natural products and therefore have been the subject of intense synthetic activity. The report summarizes recent advances in this area, with a particular focus on work published since an earlier review on the topic, in 2000 (Marzabadi, C. H.; Franck, R. W. Tetrahedron 2000, 56, 8385-8417).
Novel Heterocycloaddition Reaction of Glycals
Dios, Angeles,Geer, Aloma,Marzabadi, Cecilia H.,Franck, Richard W.
, p. 6673 - 6679 (2007/10/03)
Diacyl thione species 1 has been generated and reacted in situ with both pyranoid and furanoid glycals to form novel [4 + 2] cycloadducts. Factors such as protecting groups and configuration of substituents in the glycals along with medium effects were varied to discover influences on face selectivity and reactivity. A qualitative correlation of reactivity with the HOMO-LUMO gap between the glycal (HOMO) and the heterodienic species (LUMO) is observed. In one example, the isolation of byproducts suggests that the cycloaddition may in fact be stepwise.
Cycloaddition als Methode zur Glycosidierung
Capozzi, Giuseppe,Dios, Angeles,Franck, Richard W.,Geer, Aloma,Marzabadi, Cecilia,et al.
, p. 805 - 807 (2007/10/03)
Keywords: Cycloadditionen; Glycale; Glycoside; Thione
Phthalimidesulfenyl Chloride. 9. A Simple Access to α,α'-Dioxothiones, a New Class of Bis-heterodienes. Synthesis of 1,4-Oxathiin Systems
Capozzi, G.,Franck, R. W.,Mattioli, M.,Menichetti, S.,Nativi, C.,Valle, G.
, p. 6416 - 6426 (2007/10/03)
α,α'-Dioxothiophthalimides 4a and 4b react with pyridine to generate the α,α'-dioxothiones 5a and 5b which undergo chemo- and regiospecific inverse electron demand Diels-Alder reactions with electron-rich alkenes to give 1,4-oxathiin heterocyclic syszems.Enol ethers, silyl enol ethers, vinyl sulfides, vinyl amides, substituted styrenes, and electron rich alkynes and allenes can be fruitfully employed as dienophiles.Among the vinyl ethers tested tri-O-benzylglucal was successfully used as a dienophile.Ab initio molecular orbital calculations performed on thiones 5a and 5b as well as on a selected enol ether are consistent with the experimental results.When thione 5a was generated in the presence of 2,3-dimethyl-2-butene (31) and -(β)-pinene (33) a selective ''thiophlic ene reaction'' was observed leading to the formation of sulfides 32 and 34.Thione 5b reacted similarly with 33 to generate the sulfide 35.Additionally a competition between the dienic versus dienophilic behavior of α,α'-dioxothiones 5a and 5b was observed in reactions with 2,3-dimethoxy-1,3-butadiene (45) and 2-methoxyfuran (50).A preliminary screening of the reactivity of 1,4-oxathiins 7c and 8b, used as model substrates, is also outlined.
Phthalimidesulfenyl Chloride Part 6. The First Example of an α-Oxothione Acting as Heterodiene: Synthesis of 2,3-Dihydro-1,4-Oxathiines.
Capozzi, Giuseppe,Menichetti, Stefano,Nativi, Cristina,Rosi, Alessandro,Franck, Richard W.
, p. 4253 - 4256 (2007/10/02)
α-α'-Dioxothione 3a acts as heterodiene undergoing 4 + 2 cycloaddition reactions with enol ethers with the regiospecific formation of 2,3-dihydro-1,4-oxathiines 5 in good yields.The reaction is very simple and quite general.Using this reaction the thiosug
