Chemical and Pharmaceutical Bulletin p. 1983 - 1989 (1991)
Update date:2022-07-29
Topics:
Tsuda
Nishimura
Ito
Lithium aluminum hydride reduction of glycopyranoside-monotosylates caused three reactions: (1) stereospecific 1,2-shift, producing branched furanosides (path A), (2) reductive O-S bond cleavage, producing the original glycosides (path B), and (3) reductive removal of the tosyloxy group, producing deoxyglycosides (path C). The path A reaction was particularly evident for the monotosylates at 2-O, 3-O, and 4-O: for example, methyl 2-O-tosyl-α-D-xylopyranoside gave methyl 2-deoxy-2-C-(hydroxymethyl)-α-D-α-erythrofuranoside in 60% yield. This reaction opens a new and efficient route to branched glycofuranosides of natural and unnatural type. Stereo-electronic requirements of this reaction in relation to the balance of the other two reactions are discussed.
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