Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

Gasch, Consolación; Pradera, M. A.; Salameh, Bader A.; Molina, José Luis Malo de; Fuentes, José

doi:10.1016/s0957-4166(01)00223-3

Cited by 44 publications

(20 citation statements)

References 52 publications

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“…[11] Compound 1 was treated with azidotrimethylsilane and trimethylsilyltriflate at 0°C for 45 min to afford 2-azido trimethylsilyl ether 2a and an inseparable mixture containing 2-azido alcohol 2b and bicyclic product 2c (Scheme 1). [12] Compounds 2b and 2c have almost the same polarity and could not be separated by column chromatography. Fortunately, byproduct 2c could be isolated by repetitive precipitation using ethyl acetate leaving behind 2b in the mother liquor (see experimental section).…”

Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis of Clickable Psicofuranose Glycocarbamates and Application of Their Self‐Assembled Nanovesicles for Curcumin Encapsulation

et al. 2020

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Among the cyclic forms of carbohydrates, pyranoside derivatives have widely contributed to the well‐defined nanoassemblies. However, nanoassemblies originating from furanoside derivatives/oligomers, excluding nucleosides are underrepresented. Herein, we discuss the design and solid‐phase synthesis of homoligomers of a new class of clickable psicofuranose glycocarbamates that display nanovesicular/spherical nanostructures, an occurrence rarely observed in furanoside oligomers. The key intermediate, D‐(‐)‐fructose derived 2‐azido psicofuranose carbonate, was converted into dimeric and tetrameric azido‐glycocarbamates on solid‐phase which on subsequent “Click” reaction provided triazolyl glycocarbamates. These amphiphilic glycocarbamates self‐assembled into thermally and proteolytically stable spherical vesicles of 200‐800 nm size with visible hollow nature in CH3OH and tightly packed sphericals in CH3OH‐H2O. These nanostructures are characterized by various microscopy techniques. Effect of Cu+2 and Zn+2 ions, various cationic stimuli on the morphology of these nanostructures was studied. Hydrophobic drug curcumin was encapsulated in the hollow vesicles and release of the drug was investigated.

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Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis of Clickable Psicofuranose Glycocarbamates and Application of Their Self‐Assembled Nanovesicles for Curcumin Encapsulation

et al. 2020

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“…Thus, the exploration of carbohydrate-based oxazolines [39–40] has been limited to serve as glycosyl donors or as intermediates for N -glycan synthesis. Although, a few pyranose-based oxazoline frameworks are known [41], the corresponding furanoid spiro [42] 2-oxazolines [43] are limited, to the best of our knowledge. With our interest in the area of glycopeptides [44] and carbohydrates [45], and owing to the importance of ribosides in general and spiroribofuranoses [46] in particular for drug discovery, in this paper, we report the synthesis of spiro 2-substituted-2-oxazoline ribosides utilizing a Ritter-like reaction having the general structure 6 (Fig.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

Vangala¹,

Shinde²

2015

Beilstein J. Org. Chem.

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SummaryThe TMSOTf-mediated synthesis of β-configured spirocyclic 2-substituted-2-oxazoline ribosides was achieved using a “Ritter-like” reaction in toluene through nucleophilic addition of electron-rich nitriles to the oxacarbenium ion intermediate of 1,2;3,4-di-O-isopropylidene-β-D-psicofuranose derivatives with concomitant intramolecular trapping of the C2 hydroxymethyl group on the electrophilic nitrilium carbon. These carbohydrate-derived spirooxazolines are stable and were obtained in good yield with high stereoselectivity due to the conformational rigidity imparted by the 3,4-isopropylidene group.

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“…Due to synthetic flexibility of the isothiocyanate function 3 , glycosyl isothiocyanates are attracting much attention among the N-glycosides. Sugar isothiocyanates have been used for the synthesis of carbohydrate derivatives particularly having thiourea structure, of synthetic, biological and pharmaceutical interest [4][5][6] . Antiviral, antibacterial and antitumor agents have been prepared by reaction of glycosyl isothiocyanates with biologically active amines 7,8 .…”

Section: Introductionmentioning

confidence: 99%

Comparative Study of Microwave Induced and Conventional Synthesis of Acetylated Sugar Isothiocyanates and Related Thiocarbamides

Yadgire

Korpe

Deshmukh

2011

Journal of Chemistry

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Abstract:The synthesis of several acetylated sugar isothiocyanates have been carried out under microwave irradiation in excellent yields of products by using related bromides and lead thiocyanate in sodium dried xylene. Several acetylated sugar thiocarbamides have been synthesized by the interaction of respective acetylated sugar isothiocyanates with appropriate aryl amines under microwave irradiation.

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Isothiocyanato derivatives of sugars in the stereoselective synthesis of spironucleosides and spiro-C-glycosides

Cited by 44 publications

References 52 publications

Solid‐Phase Synthesis of Clickable Psicofuranose Glycocarbamates and Application of Their Self‐Assembled Nanovesicles for Curcumin Encapsulation

Solid‐Phase Synthesis of Clickable Psicofuranose Glycocarbamates and Application of Their Self‐Assembled Nanovesicles for Curcumin Encapsulation

Synthesis of D-fructose-derived spirocyclic 2-substituted-2-oxazoline ribosides

Comparative Study of Microwave Induced and Conventional Synthesis of Acetylated Sugar Isothiocyanates and Related Thiocarbamides

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