138512-00-2

Upstream product

• 40989-96-6 2-phenyl-2,3-dihydropyran-4-one 

Downstream Products

• 82740-79-2 (2R,4R)-2-phenyl-3,4-dihydro-2H-pyran-4-yl acetate 
• 138512-07-9 (2S,4S)-4-acetoxy-2-phenyl-2,3-dihydro-4H-pyran 

Relevant academic research and scientific papers

Synthesis of 4-oxepanones by the Lewis acid-promoted ring-expansion reaction of cyclopropapyranones

In the presence of a Lewis acid, cyclopropapyranones easily reacted with silyl enolates to give the 4-oxepanones in good yields. In this reaction, the trans-isomer was mainly obtained.

Synthesis of (±)-diospongin a: A hetero-diels-alder and c-glycosylation approach

The racemic natural product diospongin A has been prepared using a short and stereoselective sequence. Key steps include a hetero-Diels-Alder reaction and an anchimeric assistance-controlled C-glycosylation. Georg Thieme Verlag Stuttgart · New York.

Facile access to cis-2,6-disubstituted tetrahydropyrans by palladium-catalyzed decarboxylative allylation: Total syntheses of (±)-Centrolobine and (+)-decytospolides A and B

Cis-2,6-Tetrahydropyran is an important structural skeleton of bioactive natural products. A facile synthesis of cis-2,6-disubstituted-3,6-dihydropyrans as cis-2,6-tetrahydropyran precursors has been achieved in high regioand stereoselectivity with high yields. This reaction involves a palladium-catalyzed decarboxylative allylation of various 3,4-dihydro-2H-pyran substrates. Extending this reaction to 1,2-unsaturated carbohydrates allowed the achievement of challenging b-C-glycosylation. Based on this methodology, the total syntheses of (±)-centrolobine and (+)-decytospolides A and B were achieved in concise steps and overall high yields.

A synthesis of densely functionalized 2,3-dihydropyrans using ring-closing metathesis and base-induced rearrangements of dihydropyran oxides

The preparation of dihydropyran and dihydrofuran oxides and their rearrangement in the presence of lithium dialkylamides to functionalized 2,3-dihydropyrans or 2,3-dihydrofurans, respectively, is described. The regiochemical outcome of the reaction can be influenced by the relative configuration of the starting epoxides and the steric demand of the base. The 2,3-dihydropyrans obtained were converted stereoselectively to difunctionalized 3,4-dihydropyrans by the carbon-Ferrier reaction, or to fused acetals by addition of dimedone, mediated by ceric ammonium nitrate. The stereochemical results are rationalized by mechanistic proposals.

A route to artificial glycoconjugates and oligosaccharides via enzymatically resolved glycals: Dramatic effects of the handedness of the sugar domain upon the properties of an anthracycline drug

Racemic, fully synthetic glycals of considerable structural variety may be kinetically resolved via enzymatically mediated transesterification using Lipase PS-30 from Pseudomonas cepacia as catalyst and vinyl acetate as acyl donor. This methodology provid