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A general route to 4-C-branched sugars. Synthesis of methyl alpha-caryophylloside
1Institut de Pharmacologie et de Biologie Structurale du CNRS, 205 route de Narbonne, F-31077, Toulouse, France. prandi@ipbs.fr
Carbohydrate Research
|May 30, 2001
Abstract:
The total synthesis of methyl 3,6-dideoxy-4-C-(D-altro-1,3,4,5 tetrahydroxyhexyl)-alpha-D-xylo-hexopyranoside, the methyl glycoside of the recently isolated 4-C-branched sugar caryophyllose, has been completed in a stereoselective and convergent manner. The synthesis of this dodecose relies on the diiodosamarium mediated coupling of two six-carbon fragments: a cyclic ketone and an acid chloride.