Carbohydrate research

An enantiospecific synthesis of (R)-1, 4, 7-trioxaspiro [5.5] undecane from d-fructose

KH Aamlid, L Hough, AC Richardson, D Hendry

Index: Aamlid, Kai H.; Hough, Leslie; Richardson, Anthony C.; Hendry, David Carbohydrate Research, 1987 , vol. 164, p. 373 - 390

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Citation Number: 9

Abstract

Abstract Periodate oxidation of 1, 2-O-ethylene-β-d-fructopyranose and ring closure of the resulting dialdehyde with nitromethane afforded a mixture of four 4-deoxy-1, 2-O-ethylene-4- nitrohex-2-uloses having the α-l-xylo, β-d-arabino, α-l-lyxo, and β-d-ribo configurations, together with two heptuloses which arose from products of the incomplete oxidation of the starting material. When nitromethane was in excess of the base used for the cyclisation ...