Showing papers on "Glucal published in 1996"
TL;DR: Difluoroenoxysilanes, prepared from acylsilanes and trifluorsilane under fluoride activation, were glycosylated by glucal to yield C -dif-luoroglycosides with a dif-fluoromethylene group in place of the anomeric oxygen as discussed by the authors.
36 citations
21 citations
14 citations
TL;DR: In this paper, 3-O-acetyl glucal and related species with acetylperchlorate were treated with a high degree of stereocontrol at the new CC bond.
12 citations
TL;DR: Vinyl glycoside 2, available in two steps from tribenzyl glucal, is found to be an excellent glycosyl donor for the synthesis of 2-deoxy-β-glycosides as discussed by the authors.
12 citations
TL;DR: In this paper, the synthesis of (5 R, 7 S, 13 S )- and (5 S, 7 S, 13S )-13-methoxy-1,6,8-trioxadispiro[4.1.5] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7, is reported.
Abstract: The synthesis of (5 R , 7 S , 13 S )- and (5 S , 7 S , 13 S )-13-methoxy-1,6,8-trioxadispiro[4.1.5.3] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7 , is reported. The key steps for the construction of the two spiroacetal systems involved a double, step by step, radical abstraction promoted by (diacetoxyiodo)benzene and iodine.
9 citations
TL;DR: In this paper, a novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented, which helps to gain further insight into the mechanism of the well-documented hypervalent iodine-promoted allylic oxidation of cyclic enol ethers.
Abstract: The reaction of 3,4-bis(O-tert-butyldimethylsilyl)-6-O-tosyl-D-glucal 4 with the Koser reagent [PhI(OH)OTs] unexpectedly afforded tetrahydrofurfural 6 as well as 2,3-anhydropyranose 7 as major products. This unprecedented, stereoselective transformation helps to gain further insight into the mechanism of the well-documented hypervalent iodine-promoted allylic oxidation of cyclic enol ethers. A novel chemoenzymatic method for the preparation of glucal 4 in high yield is presented.
TL;DR: In this paper, the synthesis of (5 R, 7 S, 13 S )- and (5 S, 7 S, 13S )-13-methoxy-1,6,8-trioxadispiro[4.1.5] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7, is reported.
Abstract: The synthesis of (5 R , 7 S , 13 S )- and (5 S , 7 S , 13 S )-13-methoxy-1,6,8-trioxadispiro[4.1.5.3] pentadecane from tri- O -acetyl- d -glucal, by a convenient homologation of C-1 and C-6 atoms which led to an appropriate dihydroxyl intermediate 7 , is reported. The key steps for the construction of the two spiroacetal systems involved a double, step by step, radical abstraction promoted by (diacetoxyiodo)benzene and iodine.