Issue 0, 1987

Higher-carbon sugars. Part 8. The synthesis of some decitols via the epoxidation of unsaturated precursors

Abstract

Sharpless epoxidation of (E)-8,9-dideoxy-1,2 : 3,4 : 6,7-tri-O-isopropylidene-α-D-threo-D-galacto-dec-8-enopyranose (3) with di-isopropyl L-(+)-tartrate as the chiral auxiliary furnished a mixture of 8,9anhydro-1,2 : 3,4 : 6,7-tri-O-isopropylidene-β-L-galacto-D-galacto-decopyranose (10)(isolated in 63% yield) and the α-D-ido-galacto isomer (11) in the ratio ∼5 : 1. Base-catalysed hydrolysis of the epoxy alcohol (10) gave, via preferential ring-opening of the Payne-rearrangement product (12), 1,2 : 3,4 : 6,7-tri -O-isopropylidene-α-D-altro-D-galacto-decopyranose (8), which yielded Daltro-D-galacto-decitol (13) following acidic hydrolysis and reduction of the resulting decose. The epoxy alcohol (11) was the principal product obtained on Sharpless epoxidation of the decenopyranose (3) with di-isopropyl D-(–)-tartrate as the chiral auxiliary, and was similarly transformed into L-gluco-D-galacto-decitol (L-galacto-D-gulo-decitol)(16). The same strategy was also used in the synthesis of D-gluco-D-galacto-decitol (L-galacto-L-gulo-decitol)(1) and L-altro-D-galacto-decitol (25) from (E)-8,9-dideoxy-1,2 : 3,4 : 6,7-tri-O-isopropylidene-β-L-threo-D-galacto-dec-8-enopyranose (18).

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1987, 2421-2426

Higher-carbon sugars. Part 8. The synthesis of some decitols via the epoxidation of unsaturated precursors

J. S. Brimacombe, R. Hanna and A. K. M. S. Kabir, J. Chem. Soc., Perkin Trans. 1, 1987, 2421 DOI: 10.1039/P19870002421

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