Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed S(N)2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols.
A highly stereoselective synthesis of C-vinyl furanosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyation-cycloetherification reaction at the C-3 position.
Tsuchiya
Hitoshi
H
School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
Asakura
Noriaki
N
Ikeda
Yasunori
Y
Yamada
Hidetoshi
H
D002236:Carbohydrate Conformation; D002384:Catalysis; D050113:Imino Furanoses / Q000138:chemical synthesis* / Q000737:chemistry; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism; D013402:Sugar Alcohols / Q000737:chemistry*; D013816:Thermodynamics; D014753:Vinyl Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D050113:Imino Furanoses; D007202:Indicators and Reagents; D013402:Sugar Alcohols; D014753:Vinyl Compounds