Journal of Organic Chemistry p. 5646 - 5649 (1985)
Update date:2022-08-05
Topics:
Binkley, Roger W.
The reaction of methyl 6-deoxy-2,3-di-O-p-tolylsulfonyl-α-D-galactopyranoside (4) with lithium triethylborohydride (LTBH) gives three primary products, all of which result from rearrangement.One of these, methyl 5-deoxy-3-C-(hydroxymethyl)-2-O-p-tolylsulfonyl-α-D-xylofuranoside (7), arises from ring contraction while the other two, methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-xylo- (5) and -ribo-hexopyranosides (9), result from hydride migration and reduction of the resulting ketone, methyl 3,6-dideoxy-2-O-p-tolylsulfonyl-α-D-erythro-hexopyranosid-4-ulose (8).Photolysis of compounds 4, 5, and 9 removes the tosyl groups.
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Doi:10.1021/jo00352a036
(1986)Doi:10.1246/cl.1985.1589
(1985)Doi:10.1016/0022-328X(85)87253-3
(1985)Doi:10.1039/jr9610002828
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(2018)
