A Sweet Result

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Science  15 Sep 2000:
Vol. 289, Issue 5486, pp. 1843
DOI: 10.1126/science.289.5486.1843a

Sucrose is readily made by sugar cane and the sugar beet, but to organic chemists it presents a formidable challenge in the control of stereochemistry. Sucrose contains a trehalose linkage, and thus sterochemistry must be controlled at both C-1 carbon atoms that link the sugar rings (the anomeric carbons). Early efforts focused only on the α linkage to glucose; because the resulting linkage to the fructosyl acceptor was a mixture of α and β, yields were low (about 6%). Oscarson and Sehgelmeble now describe a method for synthesizing β-fructofuranosides. They lock the anomeric CH2OH group on the five-membered ring to the α side through an internal 1,4 acetyl bridge and form a thioglycoside fructose donor. This donor could then be coupled to a glucose acceptor to form sucrose in 80% overall yield. — PDS

J. Am. Chem. Soc., in press.

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