THE SYNTHESIS OF 3-HEXULOSES: PART II. DERIVATIVES OF 1-DEOXY-L-arabo-3-HEXULOSE (SYN. 6-DEOXY-L-lyxo-4-HEXULOSE)

Abstract

Oxidation of 1,3:2,5-di-O-methylene-L-rhamnitol yielded 2,5:4,6-di-O-methylene-1-deoxy-L-arabo-3-hexulose, which was characterized as its 2,5-dichlorophenylhydrazone and by reduction to derivatives of L-rhamnitol and of 6-deoxy-L-talitol. Oxidation of 2,5-O-methylene-L-rhamnitol 1-benzoate yielded a syrupy 3,4-diketose which was characterized as the crystalline quinoxaline derivative. Attempts to convert 1,2:4,5-di-O-isopropylidene-D-mannitol 6-benzoate to a ketose were unsuccessful.