Topic
Glycal
About: Glycal is a research topic. Over the lifetime, 897 publications have been published within this topic receiving 17422 citations.
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TL;DR: A variety of β-C -glycosides may be readily accessed in a stereoselective fashion from 3-OH glycal esters, via the use of Tebbe methylenation and subsequent thermal Claisen rearrangement as discussed by the authors.
Abstract: A variety of β- C -glycosides may be readily accessed in a stereoselective fashion from 3-OH glycal esters, via the use of Tebbe methylenation and subsequent thermal Claisen rearrangement. The use of carbohydrate ester substrates allows the formation of β(1→6) linked C -disaccharides.
2 citations
TL;DR: In this paper, a qualitative correlation of reactivity with the HOMO−LUMO gap between the glycal (HOMO) and the heterodienic species (HUMO) is observed.
Abstract: Diacyl thione species 1 has been generated and reacted in situ with both pyranoid and furanoid glycals to form novel [4 + 2] cycloadducts. Factors such as protecting groups and configuration of substituents in the glycals along with medium effects were varied to discover influences on face selectivity and reactivity. A qualitative correlation of reactivity with the HOMO−LUMO gap between the glycal (HOMO) and the heterodienic species (LUMO) is observed. In one example, the isolation of byproducts suggests that the cycloaddition may in fact be stepwise.
2 citations
TL;DR: In this article, a metal-free catalytic system was used for the synthesis of pseudoglycals using a wide range of alcohols including naturally bioactive compounds, with high α-selectivity.
Abstract: A mild and efficient synthesis of pseudoglycals has been developed using a metal-free catalytic system. Phosphoric acid proved to be an excellent catalyst for conversion of 2,4,6-tri-O-acetyl-d-glycal to 2,3-unsaturated O-glycosides. A wide range of alcohols including naturally bioactive compounds could be coupled with the glycal to give the desired products in good to excellent yields and with high levels of α-selectivity.
2 citations
TL;DR: Application of the Ferrier rearrangement led to a novel carbohydrate based synthetic route to 4-aminohexenoic acid viz. (R) and (S)-vigabatrin and the potential of D- glucose or D-galactose as the chiral starting materials for the synthesis of (R).
Abstract: Application of the Ferrier rearrangement led to a novel carbohydrate based synthetic route to 4-aminohexenoic acid viz. (R) and (S)-vigabatrin. The potential of D- glucose or D-galactose as the chiral starting materials for the synthesis of (R) and (S)- vigabatrin has been explored.
2 citations
TL;DR: The mechanism of this reaction likely involves the formation of an oxocarbenium ion intermediate via indium(III) Lewis acid-assisted ionization of the glycal C.3 acetate as discussed by the authors.
Abstract: 2,3-Unsaturated- C -aryl glycopyranosides are important intermediates in the synthesis of medicinally important C -aryl glycosides. Treatment of glycal acetates with triarylindiums in ether at room temperature gives good yields of C -aryl-Δ 2,3 -glycosides of predominantly α-configuration. The mechanism of this reaction likely involves the formation of an oxocarbenium ion intermediate via indium(III) Lewis acid-assisted ionization of the glycal C.3 acetate. Coupling of trivinyl- and tris(alkynyl)indiums with glycals similarly led to C -vinyl- and C -alkynyl-Δ 2,3 -glycosides in good yield.
2 citations