An Efficient Three-Step Synthesis of L-(-)-Oleandrose from (S)-(-)-Methyl Lactate

Abstract
L-(-)-Oleandrose (1; 2,6-dideoxy-3-O-methyl-arabino-hexose) was prepared in only three steps from (S)-(-)-methyl lactate and (3-butenylsulphonyl)benzene, without the use of protecting groups. A stereocontrolled reduction and a thermodynamically controlled exchange reaction afforded the required arabino configuration.

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