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Pure Appl. Chem., 2005, Vol. 77, No. 1, pp. 119-130

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.