From carbohydrates to carbocycles: radical routes via Tellurium derivatives

Barton, D. H. R.; Cámara, José Ignacio Mayordomo; Cheng, Xiaoqin; Géro, S. D.; Jaszberenyi, J. C.; Quiclet‐Sire, Béatrice

doi:10.1016/s0040-4020(01)85616-7

Cited by 28 publications

(7 citation statements)

References 73 publications

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“…Thus, D ‐ribose was transformed to the known isopropylidene derivative 6 according to the published procedure 6. Selective tosylation of 6 has previously been reported 7. We employed the reaction under slightly different conditions obtaining monotosylate 7 in 75 % yield.…”

Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Biological Activity of Azasugar‐Based CD163 Ectodomain Shedding Inhibitors

et al. 2007

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Section: Resultsmentioning

confidence: 99%

Design, Synthesis and Biological Activity of Azasugar‐Based CD163 Ectodomain Shedding Inhibitors

et al. 2007

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“…The c,d-unsaturated amide 35 was synthesised from the corresponding acid 34, prepared by protection of Dribonolactone, iodination (→ 33) and reductive fragmentation (Scheme 7). 31 Acetonide deprotection gave the corresponding 1,2-diol 36.…”

Section: Preparation Of Protected Sialic Acid Mimeticsmentioning

confidence: 99%

Synthesis of screening substrates for the directed evolution of sialic acid aldolase: towards tailored enzymes for the preparation of influenza A sialidase inhibitor analogues

et al. 2005

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The stereoselective synthesis of two epimeric screening substrates, (4R, 5R, 6R)- and (4S, 5R, 6R)-6-dipropylcarbamoyl-2-oxo-4,5,6-trihydroxy-hexanoic acid, for the directed evolution of sialic acid aldolase is described. The complementary methods relied on stereoselective indium-mediated additions of ethyl alpha-bromomethyl acrylate to functionalised aldehydes. With an alpha-hydroxy aldehyde, (2R, 3R)-2,3-dihydroxy-4-oxo butanoic acid dipropylamide, the addition was chelation controlled, and the syn product, (6R, 5R, 4S)-6-dipropylcarbamoyl-2-methylidene-4,5,6-trihydroxy-hexanoic acid ethyl ester, was obtained. In contrast, the stereochemical outcome of the addition to (2R, 3R)-N,N-dipropyl-2,3-O-isopropylidene-4-oxobutyramide was consistent with Felkin-Anh control, and the anti adduct, (4R, 5R, 6R)-6-dipropylcarbamoyl-2-methylidene-4-hydroxy-5,6-O-isopropylidene-hexanoic acid ethyl ester, was the major product. Ozonolysis and deprotection gave the screening substrates as mixtures of furanose and pyranose forms, in good yields.

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“…The unsaturated lactone 16 was prepared from the glucal derivative 15 [23] by treatment with mCPBA and BF 3 •OEt 2 at 0°C in CHCl 3 . [24] Further In an attempted synthesis of thiasugar derivatives by our multi-step, one-pot methodology, Michael acceptor 20 [25] was treated with 1 under similar reaction conditions. However, the reaction gave only the disulfide 21, resulting from Michael addition of the hydroxy group on the unsaturated ester moiety followed by disulfide bond formation at the primary carbon center (Scheme 4).…”

Section: An Intramolecular Version Of Tandem Sulfur Transfer/ Reductimentioning

confidence: 99%

Synthesis of Thioglycosides by Tetrathiomolybdate‐Mediated Michael Additions of Masked Thiolates.

2005

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Synthesis of Thioglycosides by Tetrathiomolybdate-Mediated Michael Additions of MaskedThiolates. -Thioglycosides are prepared in excellent yields under neutral conditions by use of tetrathiomolybdates as sulfur-transfer reagents. Sugar halides give by reaction with the molybdates sugar disulfides, which then undergo reductive cleavage in situ to afford the corresponding thiolates. The subsequent Michael addition with alkenes provides the desired thioglycosides. The successful application of the method in aqueous medium is demonstrated. Some inter-and intramolecular diastereoselective variants of the method are also presented. In the case of substrate (XV), the reaction is unsuccessful and a dimeric disulfide is formed. -(SRIDHAR, P. R.; PRABHU, K. R.; CHANDRASEKARAN*, S.; Eur.

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From carbohydrates to carbocycles: radical routes via Tellurium derivatives

Cited by 28 publications

References 73 publications

Design, Synthesis and Biological Activity of Azasugar‐Based CD163 Ectodomain Shedding Inhibitors

Design, Synthesis and Biological Activity of Azasugar‐Based CD163 Ectodomain Shedding Inhibitors

Synthesis of screening substrates for the directed evolution of sialic acid aldolase: towards tailored enzymes for the preparation of influenza A sialidase inhibitor analogues

Synthesis of Thioglycosides by Tetrathiomolybdate‐Mediated Michael Additions of Masked Thiolates.

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