Glycerol carbonate in Ferrier reaction: Access to new enantiopure building blocks to develop glycoglycerolipid analogues

Costa, Pollyanna Leite Ferreira da; Melo, Valentina Nascimento e; Guimarães, Bruna Martins; Schuler, Marie; Pimenta, Vanessa; Rollin, Patrick; Tatibouët, Arnaud; Oliveira, Ronaldo N. de

doi:10.1016/j.carres.2016.10.009

Cited by 6 publications

(4 citation statements)

References 40 publications

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“…The reactivity of the free hydroxyl group of 1,2‐GC has long been studied through sulfonylation, carbamate formation, ether alkylation, or esterification . Glycosylation has also been performed on glycerol carbonate by applying Ferrier conditions on glucal . 1,3‐GC also proved to be a useful synthon for fine chemistry but, while 1,2‐GC is easily prepared, its 1,3‐isomer needs a sequential approach .…”

Section: Introductionmentioning

confidence: 99%

Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

et al. 2017

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Section: Introductionmentioning

confidence: 99%

Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

et al. 2017

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“…13). The results show that α-glucoside 3 has an (S) configuration at C-4 of the carbonate aglycone [45].…”

Section: C-glycosides Have Attracted a Lot Of Attention From Research...mentioning

confidence: 92%

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Filho,

Freitas,

Freitas

et al. 2024

IRJPAC

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Determination of the stereochemistry of the stereocenter from the aglyconic part of carbohydrates is always one of the most important tasks for chemistry carbohydrates researchers. The absolute configuration (AC), a challenge for synthetic chemists, has attracted much attention. During the past few decades, many techniques and approaches have been developed to determine the AC of carbohydrates, including methods of X-ray diffraction (XRD), electronic and vibrational circular dichroism (ECD and VCD), Raman optical activity (ROA), nuclear magnetic resonance (NMR) utilizing anisotropic effects of chiral derivatizing agents, and quantum chemical calculations. On the other hand, none of the currently applied techniques can dominate AC determination, since they each have their respective limitations corresponding to the different structural features. This review summarizes most of the techniques and methods commonly used in AC assignment of carbohydrates (but specifically glycosides), in the last decades (2000-2023). GRAPHICAL ABSTRACT

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“…Among the valuable derivatives, which can be easily prepared from glycerol, 4‐hydroxymethyl‐1,3‐dioxolan‐2‐one, known as glycerol‐1,2‐carbonate (GC), is particularly attractive as an environmentally benign solvent [1] but also as a synthetic intermediate with diversified reactivity [2–4]. The polymorphic chemical versatility of GC was earlier documented by us, either as such [5–7] or under activated forms presenting additional electrophilic reactivity [8]. Namely, by reacting sulfonylated GCs with aza‐aromatic structures containing an acidic NH bond, we investigated new molecular hybrids in which the aryl system is N ‐connected to a glyceryl‐derived appendage [9].…”

Section: Introductionmentioning

confidence: 99%

Glycerol‐1,2‐carbonate: A mild reagent for the N‐glycerylation of pyrazolecarboxylates

Zagorskytė,

Bieliauskas,

Pukalskienė

et al. 2023

Journal of Heterocyclic Chem

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In this study, glycerol‐1,2‐carbonate was employed as a convenient reagent for the synthesis of more complex pyrazole‐containing heterocyclic systems. 3‐O‐Tosylated glycerol‐1,2‐carbonate (TGC) was used for alkylation of NH‐pyrazolecarboxylates. The obtained N‐glycerylated pyrazoles were further treated with diverse nucleophiles for 2‐oxo‐1,3‐dioxolane ring cleavage. The synthesized 1‐(2,3‐dihydroxypropyl)‐1H‐pyrazole‐5‐carboxylates were subsequently hydrolyzed and treated with p‐toluenesulfonic acid, yielding a series of 6‐(hydroxymethyl)‐6,7‐dihydro‐4H‐pyrazolo[5,1‐c][1,4]ox‐azin‐4‐ones.

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Glycerol carbonate in Ferrier reaction: Access to new enantiopure building blocks to develop glycoglycerolipid analogues

Cited by 6 publications

References 40 publications

Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

Activated Glycerol Carbonates, Versatile Reagents with Aliphatic Amines: Formation and Reactivity of Glycidyl Carbamates and Trialkylamines

Absolute Configuration Determination of Sugar: A Review of the Different Methods

Glycerol‐1,2‐carbonate: A mild reagent for the N‐glycerylation of pyrazolecarboxylates

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