Journal of Organic Chemistry p. 5257 - 5264 (1989)
Update date:2022-09-26
Topics:
Andrews, Mark A.
Gould, George L.
Klaeren, Stephen A.
Unprotected Cn aldose sugars are cleanly decarbonylated by 1 equiv of chlorotris(triphenylphosphine)rhodium(I) in 1-24 h at 130 deg C in N-methyl-2-pyrrolidinone solution to give the corresponding Cn-1 alditol in about 75-95percent yields.This technique represents a useful variation on traditional carbohydrate "descent of series" reactions.The procedure is quite general and also works on a number of aldose derivatives, such as deoxy sugars, N-acetylated amino sugars, and disaccharides, providing convenient small-scale syntheses of deoxyalditols, (acetylamino)deoxyalditols, and glycosylalditols, respectively.The reactions proceed with complete retention of stereochemistry, the only side products observed being a few percent of the Cn lactones and the Cn-2 alditol.Attempts to make the reactions catalytic have not yet been very successful.
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