Stereoselective Synthesis and Immunogenic Activity of the <i>C</i>-Analogue of Sulfatide

Modica, Emilia; Compostella, Federica; Colombo, Diego; Franchini, L.; Cavallari, Marco; Mori, Lucia; Libero, Gennaro De; Panza, Luigi; Ronchetti, Fiamma

doi:10.1021/ol061100y

Cited by 20 publications

(15 citation statements)

References 30 publications

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“…271 Both the β-Cand β-O-glycosides of sulfatide 14 have been synthesized. 272 A Wittig sigmatropic rearrangement was followed by a Horner−Wadsworth− Emmons olefination (HWE) to install the Sph backbone for the stereoselective synthesis of derivative 13 over 13 steps. This was followed by regioselective sulfation of Gal to provide 14.…”

Section: Chemical Synthesis Of Cerebrosides Sulfatides and Derivativesmentioning

confidence: 99%

“…Various β- C- and β -O- glycoside GalCer analogues have been synthesized, many of which were tested as inhibitors of HIV infection. − For example, sulfatide 12 was synthesized in five steps via glycosylation of azidosphingosine with a trichloroacetimidate donor . Both the β- C- and β -O- glycosides of sulfatide 14 have been synthesized .…”

Section: Chemical Synthesis Of Glycolipidsmentioning

confidence: 99%

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Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

et al. 2018

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The plasma membrane of cells contains a diverse array of lipids that provide important structural and biological features. Glycolipids are typically a minor component of the cell membrane and consist primarily of glycosphingolipids (GSLs). GSLs in vertebrates contain a multifarious assortment of glycan headgroups, which can be important to biological functions based on lipid-lipid and lipid-protein interactions. The design of probes to study these complex targets requires advanced synthetic methodologies. In this Review, we will discuss recent advances in chemical and chemoenzymatic synthesis of GSLs in conjunction with the use of these approaches to design new probes. Examples using either chemical or enzymatic semisynthesis methods starting from isolated GSLs will also be reviewed. Focusing primarily on vertebrate glycolipids, we will highlight examples of radionuclide, fluorophore, photoresponsive, and bioorthogonal tagged GSL probes.

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Section: Chemical Synthesis Of Cerebrosides Sulfatides and Derivativesmentioning

confidence: 99%

Section: Chemical Synthesis Of Glycolipidsmentioning

confidence: 99%

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

et al. 2018

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“…The reaction can also be performed as a one-pot procedure, with analogous results. However, in the synthesis of a C-analogue of suphated galactosylceramide [67], HWE reaction between sugar derived dimethylphosphonoketone 39a and tetradecanal gave exclusively the E-alkene 39b in 71% yield, showing that substrate structure and reaction conditions may in some cases overcome poor reactivity of long chain aldehydes (Scheme 39).…”

Section: Lipidsmentioning

confidence: 99%

Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products

Bisceglia¹,

Orelli

2012

COC

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The Horner-Wadsworth-Emmons reaction has evolved in the last years as one of the most powerful and reliable method for stereocontrolled olefin synthesis. The reaction has become a widespread standard tool in natural products total syntheses, providing access to relatively simple as well as highly complex synthetic targets. In this work we present the most representative applications within the field of natural product synthesis from 2000 to the present year. The examples comprise the synthesis of macrocycles, 5 to 7 membered rings, lipids and related compounds, alkaloids and cyclic ethers. They were chosen from a large amount of literature reports and illustrate the use of the HWE reaction in the synthesis and elaboration of key intermediates and in the crucial assembly of highly functionalized synthetic precursors.

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“…However, the reports on the execution of WR on a carbohydrate-derived framework are minimal. In this connection, the [1,2]- − or [2,3]- − WR of carbohydrate acetals has been studied to convert the O -glycosides into C -glycosides. Recently, the application of WR on pyranose-derived allyl propargyl ethers was reported …”

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confidence: 99%

[1,2]- vs [2,3]-Wittig Rearrangement in Carbohydrate Derived Alkenyl Systems

2021

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A simple and efficient strategy for the regio- and stereoselective synthesis of carbon-branched sugar derivatives is described. The successful implementation of Wittig rearrangement on substrates derived by Ferrier rearrangement of various glycals and 3-O-alkenyl glycals is studied extensively. A highly selective [1,2]- or [2,3]-Wittig rearrangement is revealed that provides a novel class of stereodefined 3-C-branched glycals and C-glycosides, which are otherwise difficult to obtain.

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Stereoselective Synthesis and Immunogenic Activity of the C-Analogue of Sulfatide

Cited by 20 publications

References 30 publications

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

Synthetic Strategies for Modified Glycosphingolipids and Their Design as Probes

Recent Applications of the Horner-Wadsworth-Emmons Reaction to the Synthesis of Natural Products

[1,2]- vs [2,3]-Wittig Rearrangement in Carbohydrate Derived Alkenyl Systems

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