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- W2040993457 abstract "The known 3-O-benzyl-D-xylose was converted into methyl (4R,5R,6R)-4,6,7-triacetoxy-5-benzyloxy-2-(methoxycarbonyl)heptanoate (8) by employing Knoevenagel condensation of 2,4,5-tri-O-acetyl-3-O-benzyl-aldehydo-D-xylose with dimethyl malonate as a key reaction. O-Deacetylation of 8 and successive glycol cleavage followed by acetylation gave a mixture of (1S,4R,5R,6R)-5-acetoxy-6-benzyloxy-4-methoxycarbonyl-2-oxobicyclo[2.2.1]heptan-3-one and dimethyl (2R,3R,4S)-2,4-diacetoxy-3-benzyloxy-1,1-cyclopentanedicarboxylate (12), which was converted into 12 exclusively. This enantiomerically pure highly oxygenated cyclopentane dicarboxylate 12 was converted into (3S,4S)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene (15) by 1) thermal demethoxycarbonylation accompanied by β-elimination of the acetoxyl group, 2) diisobutylaluminium hydride reduction, and 3) selective protection of thus formed 1-cyclopentene-1-methanol. Pyridinium chlorochromate oxidation of 15 followed by reduction with sodium borohydride gave a 6.4:1 mixture of (3S,4R)-3-benzyloxy-1-(t-butyldiphenylsilyloxymethyl)-4-hydroxy-1-cyclopentene (18) and 15. Hydroboration of O-desilyl derivative of 18 proceeded stereoselectively from the less hindered α-face, and (1R,2R,3R,4R)-2,4-diacetoxy-1-acetoxymethyl-3-(benzyloxy)cyclopentane (21) was obtained after acetylation. Deprotection of 21 gave pseudo-β-D-arabinofuranose." @default.
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- W2040993457 date "1987-10-01" @default.
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- W2040993457 title "Transformation of D-Xylose to (1<i>R</i>,2<i>R</i>,3<i>R</i>,4<i>R</i>)-2,3,4-Trihydroxy-1-(hydroxymethyl)cyclopentane, Pseudo-β-D-arabinofuranose" @default.
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- W2040993457 doi "https://doi.org/10.1246/bcsj.60.3673" @default.
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