Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents

Gómez, Ana M.; Casillas, Marta; Rodrı́guez, Benjamı́n; Valverde, Serafı́n; López, J. Cristóbal

doi:10.3998/ark.5550190.0011.324

Cited by 3 publications

(4 citation statements)

References 3 publications

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“…Treatment of ether- and/or acetal-protected glycosyl chlorides with phenyllithium even combined both processes, the chlorides 87 – 90 being converted to 1- C -phenyl glycals 91 – 94 in good yields (Scheme ). , …”

Section: Synthesis Of C-glycosylation Of Arenesmentioning

confidence: 99%

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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This Review summarizes close to 500 primary publications and surveys published since 2000 about the syntheses and diverse bioactivities of C-glycopyranosyl (het)arenes. A classification of the preparative routes to these synthetic targets according to methodologies and compound categories is provided. Several of these compounds, regardless of their natural or synthetic origin, display antidiabetic properties due to enzyme inhibition (glycogen phosphorylase, protein tyrosine phosphatase 1B) or by inhibiting renal sodium-dependent glucose cotransporter 2 (SGLT2). The latter class of synthetic inhibitors, very recently approved as antihyperglycemic drugs, opens new perspectives in the pharmacological treatment of type 2 diabetes. Various compounds with the C-glycopyranosyl (het)arene motif were subjected to biological studies displaying among others antioxidant, antiviral, antibiotic, antiadhesive, cytotoxic, and glycoenzyme inhibitory effects.

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Section: Synthesis Of C-glycosylation Of Arenesmentioning

confidence: 99%

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

et al. 2017

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“…The 3,6-anhydro derivative of the methyl α- d -glucopyranoside ( 41 ) [ 38 ] was identified as the main product, which was formed in excellent yield (80%). We also attempted to prepare the unprotected derivative from the 6-OTs derivative of phenyl 1-thio-α- d -mannopyranoside ( 42 ) [ 39 , 40 ]. We tested two types of reaction conditions (a, CH 3 CN + DBU and b, DMF + DBU), but unfortunately neither of the reactions produced the expected product.…”

Section: Resultsmentioning

confidence: 99%

“…Reaction 1 : To the solution of compound 42 [ 39 , 40 ] (483 mg, 1.134 mmol) in dry CH 3 CN (6.8 mL), DBU (1018 μL, 6.804 mmol, 6.0 equiv.) was added.…”

Section: Methodsmentioning

confidence: 99%

First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity

Demeter

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et al. 2023

IJMS

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The emergence of drug-resistant bacteria and fungi represents a serious health problem worldwide. It has long been known that cationic compounds can inhibit the growth of bacteria and fungi by disrupting the cell membrane. The advantage of using such cationic compounds is that the microorganisms would not become resistant to cationic agents, since this type of adaptation would mean significantly altering the structure of their cell walls. We designed novel, DBU (1,8-diazabicyclo[5.4.0]undec-7-ene)-derived amidinium salts of carbohydrates, which may be suitable for disturbing the cell walls of bacteria and fungi due to their quaternary ammonium moiety. A series of saccharide-DBU conjugates were prepared from 6-iodo derivatives of d-glucose, d-mannose, d-altrose and d-allose by nucleophilic substitution reactions. We optimized the synthesis of a d-glucose derivative, and studied the protecting group free synthesis of the glucose-DBU conjugates. The effect of the obtained quaternary amidinium salts against Escherichia coli and Staphylococcus aureus bacterial strains and Candida albicans yeast was investigated, and the impact of the used protecting groups and the sugar configuration on the antimicrobial activity was analyzed. Some of the novel sugar quaternary ammonium compounds with lipophilic aromatic groups (benzyl and 2-napthylmethyl) showed particularly good antifungal and antibacterial activity.

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“…Interestingly, treatment of permethyl-, perbenzyl-, and isopropylidene-protected pyranosyl and furanosyl chlorides 34 – 37 with alkyl or phenyl lithium reagents led to C-1 alkyl/aryl glycals 38 – 49 in good yields (Scheme ), − wherein the resultant C -glycosides underwent deprotonation at the anomeric position and subsequent elimination of the 2-ether substituent.…”

Section: C-glycosylation With Glycosyl Halidesmentioning

confidence: 99%

Recent Advances in the Chemical Synthesis of C-Glycosides

2017

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Advances in the chemical synthesis of C-pyranosides/furanosides are summarized, covering the literature from 2000 to 2016. The majority of the methods take advantage of the construction of the glycosidic C-C bond. These C-glycosylation methods are categorized herein in terms of the glycosyl donor precursors, which are commonly used in O-glycoside synthesis and are easily accessible to nonspecialists. They include glycosyl halides, glycals, sugar acetates, sugar lactols, sugar lactones, 1,2-anhydro sugars, thioglycosides/sulfoxides/sulfones, selenoglycosides/telluroglycosides, methyl glycosides, and glycosyl imidates/phosphates. Mechanistically, C-glycosylation reactions can involve glycosyl electrophilic/cationic species, anionic species, radical species, or transition-metal complexes, which are discussed as subcategories under each type of sugar precursor. Moreover, intramolecular rearrangements, such as the Claisen rearrangement, Ramberg-Bäcklund rearrangement, and 1,2-Wittig rearrangement, which usually involve concerted pathways, constitute another category of C-glycosylations. An alternative to the C-glycosylations is the formation of pyranoside/furanoside rings after construction of the predetermined glycosidic C-C bonds, which might involve cyclization of acyclic precursors or D-A cycloadditions. Throughout, the stereoselectivity in the formation of the resultant C-glycosidic linkages is highlighted.

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Synthesis of furanoid and pyranoid C-1 aryl glycals by reaction of glycosyl chlorides with organolithium reagents

Abstract: Furanosyl and pyranosyl chlorides react with aryllithium derivatives, obtained by directed ortholithiation of activated arenes, to give C-1 aryl glycals in moderate yields.

Cited by 3 publications

References 3 publications

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential

First Synthesis of DBU-Conjugated Cationic Carbohydrate Derivatives and Investigation of Their Antibacterial and Antifungal Activity

Recent Advances in the Chemical Synthesis of C-Glycosides

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