Samariumdiiodid‐vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal‐ oder ‐anion‐Acceptoren – Synthese von C‐Glycosiden

Hung, Shang‐Cheng; Wong, Chi‐Huey

doi:10.1002/ange.19961082225

Cited by 10 publications

(1 citation statement)

References 51 publications

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“…To complete the range of substrates, the glucoside 38 was extended to the thioenol ether 39 via the standard Suzuki protocol. This substrate can be considered an extreme case because oxonium ion formation as well as ring flipping are disfavored in comparison to the other pyranoside substrates (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Acetal−Vinyl Sulfide Cyclization on Sugar Substrates: Effect of Structure and Substituent

Sasmal

Maier

2002

J. Org. Chem.

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A range of 2-deoxyfuranoside and -pyranoside derivatives were fashioned into derivatives that carry a vinyl or propenyl side chain. Extension of the alkene by a Suzuki cross-coupling reaction with 1-bromo-1-(phenylthio)ethene gave thioenol ethers as the cyclization substrates. The treatment of these substrates with BF(3).Et(2)O in tert-butylmethyl ether below 0 degrees C induced cyclization to optically active bicyclic ethers. If the cyclizations are carried out in toluene as the solvent, the isomerization of the terminal thioenol ether to the inner thioenol ether can take place prior to the cyclization. The cyclization reactions can be impeded by steric and electronic factors. The opening of the bicyclic ethers could be illustrated with the base-induced conversion of the ketone 53 to the cyclooctenone 54.

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Section: Resultsmentioning

confidence: 99%

Acetal−Vinyl Sulfide Cyclization on Sugar Substrates: Effect of Structure and Substituent

Sasmal

Maier

2002

J. Org. Chem.

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Stereoselective Synthesis ofcarba- andC-Glycosyl Analogs of Fucopyranosides

Carpintero¹,

Jaramillo²,

Fernández-Mayoralas³

2000

Eur. J. Org. Chem.

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Fucopyranoside analogs with methylene groups instead of endo-or exo-anomeric oxygens, carba-and C-fucopyranosides, respectively, were synthesized. For the synthesis of 5acarba-L-fucose (1) two approaches were studied, which shared a common cyclitol building block (8), obtained from a SmI 2 -promoted carbocyclization of a D-mannitol derivative. The first route made use of a Stork radical cyclization onto a conduritol derivative 13 as the key step, which failed to give the silyl ether ring. The second route furnished the target 1, and involved regioselective elimination of a cyclic sulfate 9,

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Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars

Chiara

Sesmilo

2002

Angew. Chem.

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Samariumdiiodid‐vermittelte Kupplung von Glycosylphosphaten mit Kohlenstoffradikal‐ oder ‐anion‐Acceptoren – Synthese von C‐Glycosiden

Cited by 10 publications

References 51 publications

Acetal−Vinyl Sulfide Cyclization on Sugar Substrates: Effect of Structure and Substituent

Acetal−Vinyl Sulfide Cyclization on Sugar Substrates: Effect of Structure and Substituent

Stereoselective Synthesis ofcarba- andC-Glycosyl Analogs of Fucopyranosides

Samarium Diiodide-Mediated Reductive Coupling of Epoxides and Carbonyl Compounds: A Stereocontrolled Synthesis of C-Glycosides from 1,2-Anhydro Sugars

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