Pure Appl. Chem., 2005, Vol. 77, No. 1, pp. 119-130
doi:10.1351/pac200577010119
From 3,3,4,4-tetraethoxybutyne to carbohydrate mimics*
Leiv K. Sydnes‡, Ole H. Kvernenes, and Stig Valdersnes
Department of Chemistry, University of Bergen, Allégt. 41, NO-5007 Bergen, Norway
Abstract:
3,3,4,4-Tetraethoxy-1-butyne, available in high yield in four simple steps from ethyl vinyl ether, is a highly functionalized alkyne, which appears to be a versatile starting material for the synthesis of a range of alkylated, more-or-less deoxygenated carbohydrate mimics. However, many of the reactions used to achieve extension and subsequent structural modification of the carbon chain as well as removal of the protecting groups turn out to be rather sensitive to the substituents’ steric and electronic influence. As a result, the reactivity pattern that emerges is somewhat complex.
Keywords: alkynes; carbohydrate analogs; cyclopropanes; protecting groups; reduction; ring opening.
*Paper based on a presentation at the 24th International Symposium on the Chemistry of Natural Products and the 4th International Congress on Biodiversity, held jointly in Delhi, India, 26-31 January 2004. Other presentations are published in this issue, pp. 1-344.