Showing papers on "Ferrier rearrangement published in 1995"
75 citations
TL;DR: In this paper, a simple and convenient method for the synthesis of aryl-3,4,6-tri-O-benzyl-2-deoxy-methylene-hexopyranosides 5,6 and 7, glycosides which are not accessible by the conventional Ferrier rearrangement, has been described based on the Mitsunobu reaction of alcohols 3 and 4 with substituted phenols.
32 citations
TL;DR: In this paper, 2,5- cis substituted tetrahydro-and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach.
Abstract: Phosphonate derivatives of 2,5- cis substituted tetrahydro- and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4- trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5- cis -dihydro-2 H -pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5- cis -dihydro-2 H -pyranyl nucleosides.
15 citations
TL;DR: A synthetic program aimed to proxide access to the hitherto unknown partially protected 6-deoxy-cyclitols 8 and 9, appropriate precursors of a variety of chiral deoxy-inositol phosphates has been envisaged from the chiralDeoxy-inososes 6 and 7 which could be obtained by mercury(II) mediated carbohydrate-inosose Ferrier rearrangement.
12 citations
TL;DR: In this article, a short and facile entry to the 2, 3-unsaturated O-aryl glyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
Abstract: A short and facile entry to the 2, 3-unsaturated O-arylglyco sides via microwave induced Ferrier rearrangement of acetylated glucal is reported.
2 citations
TL;DR: In this paper, 2,5- cis substituted tetrahydro-and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach.
Abstract: Phosphonate derivatives of 2,5- cis substituted tetrahydro- and dihydro-2 H -pyranyl nucleosides have been synthesized following a stereocontrolled approach. The key step in the synthetic pathway is the introduction of the phosphonomethoxy moiety on pentopyranosyl glycals through a Ferrier-type rearrangement, yielding the 1,4- trans phosphonomethyl glycosides as the major isomers. The heterocyclic base has then been incorporated following a Mitsunobu-type condensation reaction, to obtain the 2,5- cis -dihydro-2 H -pyranyl nucleosides. The tetrahydropyranyl analogues have been prepared through hydrogenation of 2,5- cis -dihydro-2 H -pyranyl nucleosides.
TL;DR: In this article, cyclic and linear peptides are O-glycosylated by 3-(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement.
Abstract: Cyclic and linear peptides are stereoselectively O-glycosylated by 3-(acylamino)glycals through activation with TMS triflate (trimethylsilyl trifluoromethanesulfonate) without Ferrier rearrangement. The yields of the 2-deoxy-α-O-glycosides obtained range from 18 to 95%.