Lithium aluminum hydride, reduction chlorodeoxy sugars

An investigation of the reduction of chlorodeoxy sugars with lithium aluminum hydride has been reported.68 In one experiment, 3-deuterio-l,2 5,6-di-0-isopropylidene-a-D-allofuranose (197) was prepared, and converted into 3-chloro-3-deoxy-3-deuterio- l,2 5,6-di-0-isopropyl-idene-a-D-glucofuranose (198) by treatment with triphenylphos-phine-carbon tetrachloride reduction with lithium aluminum hydride gave 3-deoxy-3-deuterio-1,2 5,6-di-O-isopropylidene-a-D-r/foo-hexofuranose (199), a result which established that the reduction must have occurred with, retention of configuration at C-3. 

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