C. Yuan, R. Hollingsworth
Oct 19, 2011
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0
Influential Citations
11
Citations
Journal
Tetrahedron Letters
Abstract
Abstract The important d -glucose and d -glucose 6-phosphate analogues 1,5-anhydro- d -glucitol and 1,5-anhydro- d -glucitol 6-phosphate were prepared from methyl- d -glucoside in high yield and purity. Protecting of the hydroxyl groups as their allyl ether followed by reductive cleavage of the glycosidic linkage with triethylsilane formed the protected anhydroglucitol. No ring rearrangement or ring contraction was observed during the reduction step. Using the PdCl 2 –CuCl 2 –activated charcoal system, the allyl ether bond was cleaved with a low loading of the catalyst (0.0025 equiv per allyl group). 1,5-Anhydro- d -glucitol 6-phosphate was prepared by the phosphylation of 1,5-anhydro- d -glucitol.