Catalysis by mercuric ion of reactions of glycals with water☆
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Cited by (138)
Metal free synthesis of 2,3-dideoxy-α, β-unsaturated carbohydrate enals (Perlin aldehydes)
2023, Carbohydrate ResearchStereoselective total synthesis of penaresidin A starting from d-galactal
2014, Tetrahedron LettersGlycosyl hydroperoxides
2013, Carbohydrate ResearchCitation Excerpt :This prompted us to use sugars with an activated anomeric substituent. To this end we employed the well-known Schmidt’s trichloroacetimidates 4–6 obtained by the known procedures.10 Previously used methods based on: 50% hydrogen peroxide and molybdenum trioxide, proposed by Snatzke and co-workers4 and Taylor and co-workers,5 hydrogen peroxide in dioxane in the presence of concentrated sulfuric acid or a solution of hydrogen peroxide in tert-butanol2 when applied to imidates 4–6 did not provide the expected hydroperoxides.
InCl<inf>3</inf>-CH<inf>3</inf>CN-H<inf>2</inf>O: An efficient catalyst-solvent combination for the synthesis of Perlin aldehydes and related compounds. Application in the synthesis of unnatural l-azasugars
2011, TetrahedronCitation Excerpt :Examples of such compounds include alkyl-hex-2-eno-uloses,2 2-C-formyl glycals,3 2,3-dideoxy-α,β-unsaturated sugar aldehydes4,5 and other carbohydrate based enones.6 Since last three decades, 2,3-dideoxy-α,β-unsaturated sugar aldehydes, popularly known as Perlin aldehydes, have been serving as attractive precursors for the synthesis of a wide array of biologically important natural and unnatural compounds.7–20 Conventionally, Perlin aldehydes are prepared by oxymercuration–demercuration reaction of suitably protected glycals in the presence of 5mM sulfuric acid (Scheme 1).4
Diastereoselective Synthesis of Carbohydrate Conjugates: Pyrano[3,2- c ]quinolones
2023, Synthesis (Germany)
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Presented at the 42e Congrès, A.C.F.A.S., Quebec, Canada, May 1974.