1,2-O-Isopropylide`ne-pentodialdofuranoses

Gentile, Bernard; Ojha-Poncet, Joe ̄lle; Moret, Gilles; Schwarzenbach, D.; Barbalat-Rey, Françoise; Tronchet, J. M. J.

doi:10.1016/s0008-6215(00)83295-4

Cited by 27 publications

(9 citation statements)

References 15 publications

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“…D-Glucose may be used as a chiral template for the synthesis of (2 S ,3 R )- 2 since configurations at C3 and C4 in the hexose are retained in the target compound. The disclosed strategy relied on prior transformation of D-glucose into azidofuranoside 57 [66] and next to acid 58 . Homologation of acid 58 was accomplished by the Arndt–Eistert reaction to give the methyl ester 59 from which benzyl ester 60 was obtained for easy hydrogenolytic removal in the last step.…”

Section: Reviewmentioning

confidence: 99%

Synthesis of nonracemic hydroxyglutamic acids

Piotrowska¹,

Głowacka²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

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Glutamic acid is involved in several cellular processes though its role as the neurotransmitter is best recognized. For detailed studies of interactions with receptors a number of structural analogues of glutamic acid are required to map their active sides. This review article summarizes syntheses of nonracemic hydroxyglutamic acid analogues equipped with functional groups capable for the formation of additional hydrogen bonds, both as donors and acceptors. The majority of synthetic strategies starts from natural products and relies on application of chirons having the required configuration at the carbon atom bonded to nitrogen (e.g., serine, glutamic and pyroglutamic acids, proline and 4-hydroxyproline). Since various hydroxyglutamic acids were identified as components of complex natural products, syntheses of orthogonally protected derivatives of hydroxyglutamic acids are also covered.

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Section: Reviewmentioning

confidence: 99%

Synthesis of nonracemic hydroxyglutamic acids

Piotrowska¹,

Głowacka²,

Wróblewski³

et al. 2019

Beilstein J. Org. Chem.

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“…27,28 (2S,3R,6S)-6-Methyl-3-hydroxypipecolic acid (50), a new inhibitor of glycosidases, was prepared for the first time using such a strategy. 28 The known aldehyde 46 29 mixture of Z and E isomers in 87% yield. High-pressure hydrogenation of 47 resulted in reduction of the alkene and azide moieties as well as effecting the key reductive amination reaction.…”

Section: From Carbohydratesmentioning

confidence: 99%

Asymmetric Synthesis of Pipecolic Acid and Derivatives

Cant

Sutherland

2012

Synthesis

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The nonproteinogenic α-amino acid, L-pipecolic acid and its derivatives are components of a wide range of pharmacologically active compounds. The significant biological activity of these compounds has resulted in the development of many synthetic approaches for their preparation. This review highlights these key methods as well as the application of these compounds for the preparation of enzyme inhibitors, conformationally restricted building blocks and peptidomimetics.

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“…C 60,51 H 7,31% (16). A partir de 1,4 g (3,22 mmol) de dibromoenose 9, trait6 comme decrit pour la preparation de 15, on obtient 286 mg (32%) de 16: Rf 0,63 (hexaneIEt20 1: I); sirop; V@' 3,4; [a] 1 H, H-C(1)); 7,32 (m,5 H ,9,M'),259 (5,. 216 (31, 133 (31, 129 (loo), 123 (3).…”

Section: M~thyl-dibromo-66-dide'soxy-56-o-isopropylidzne-23-~-~-runclassified

“…A partir de 2,6 g (1 mmol) de 7 1191 traitt comme dkcrit pour la preparation de 11, on obtient 3,84 g (93%) de 14: Rf 0,55 (hexaneIEt20 2: 1); F. 53-54" (dtc. );4" (c=0,9, CHCI3).-UV. (EtOH): 213 (5940).…”

unclassified

Préparation de dérivés de sucres acétyléniques terminaux et d'acides ynuroniques par réaction de Wittig. Note de laboratoire

Tronchet

Bonenfant

Perret

et al. 1980

Helvetica Chimica Acta

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The method described for the preparation of terminal acetylenic sugars presents two advantages over earlier procedures: no new asymmetric center is created and the chain can be extended by one or more C-atoms. The method also allows preparation of ynuronic acids. The aldehydosugars derivatives 1-7 gave in good to excellent yields the corresponding gem-dibromoenoses 8-14 from which either the terminal acetylenic sugars derivatives 15-21 or the ynuronic acids 22-24 were easily prepared. A few examples of 1,3-dipolar cycloadditions (leading to 28-30) with these acetylenic sugar derivatives are also described.

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1,2-O-Isopropylide`ne-pentodialdofuranoses

Cited by 27 publications

References 15 publications

Synthesis of nonracemic hydroxyglutamic acids

Synthesis of nonracemic hydroxyglutamic acids

Asymmetric Synthesis of Pipecolic Acid and Derivatives

Préparation de dérivés de sucres acétyléniques terminaux et d'acides ynuroniques par réaction de Wittig. Note de laboratoire

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