Recent advances in photoinduced glycosylation: oligosaccharides, glycoconjugates and their synthetic applications

Sangwan, Rekha; Mandal, Pintu Kumar

doi:10.1039/c7ra01858d

Cited by 43 publications

(22 citation statements)

References 152 publications

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“…We also included commercially available eosin Y ( C ) in our studies of this ArOH‐type photoacid catalysis. We herein describe these studies, which led to the development of a direct, visible‐light‐induced photoactivation method for the catalytic stereoselective conversion of glycals into 2‐deoxyglycosides.…”

Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

2018

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The direct, photoacid-catalyzed synthesis of 2-deoxyglycosides from glycals is reported. A series of phenol-conjugated acridinium-based organic photoacids were rationally designed, synthesized, and studied alongside the commercially available phenolic catalyst eosin Y. In the presence of such a photoacid catalyst and light, synthetic glycals were activated and coupled with a range of alcohols to afford 2-deoxyglycosides in good yields and with excellent α-selectivity.

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Section: Methodsmentioning

confidence: 99%

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

2018

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“…The two acetonide protecting groups were removed under acidic condition using Dowex H + resin in aqueous THF to obtain C- In the 1 H-NMR (500 MHz, CDCl 3 ) spectrum of 5, the anomeric proton appeared as a doublet at 4.52 ppm with a coupling constant of 9.0 Hz, confirming the β-linkage. The formation of the compound was further confirmed by 1 H-1 H COSY, 13 C-NMR and ESI-MS HRMS spectral data. The methodology of synthesising 1,3-difunctionalized glycoconjugates was further extended to the preparation of other glycoconjugates, such as the α-linked C-3 O-propargylated glycolipid.…”

Section: Resultsmentioning

confidence: 72%

“…8,9 The presence of a multiple number of chiral centres and the different relative orientation of the hydroxyl groups with respect to each other make carbohydrates a source of chiral backbones that can easily be diversely functionalized with the help of selective protection and deprotection methods. [10][11][12][13] Carbohydrates are frequently used for the synthesis of various structurally diverse biomolecules, such as multivalent compounds and glycoamino acid mimics. Compared to monofunctionalized glycoconjugates, multifunctionalized glycoconjugates with different functional groups in the same sugar moiety have a better binding affinity with various bacteria, virus or lectins.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

Sahoo

Singhamahapatra

Sahoo

2018

JSCS

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A series of novel 1,3-difunctionalized glycoconjugates were synthesized using a sequence of regioselective functionalization and stereoselective glycosidation of D-glucose and D-GlcNAc. Regioselective C-3 functionalization of sugar molecules was achieved by chemical functionalization of isopropylidene or oxazoline protected sugar derivatives. The structural diversity at the anomeric carbon was explored by stereoselective chemical glycosidation. The oxazoline protected D-GlcNAc derivative gave either pyranose or furanose derivatives on glycosidation depending on the amount of Lewis acid used. The diversely functionalized glycoconjugates with azide or alkyne groups are potentially useful for the synthesis of multifunctionalized complex glycoconjugates via click reactions.

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“…Chemists have long utilized ultraviolet (UV) light irradiation to perform glycosylation. The light energy either cleaves the aglycone directly to activate the donor, or is harvested by a photosensitizer for further activation …”

Section: Photochemical Reactionsmentioning

confidence: 99%

Recent Developments in Stereoselective Chemical Glycosylation

Ling

Bennett

2019

Asian J Org Chem

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Because of their pivotal biological functions, attention to sugars and glycobiology has grown rapidly in recent decades, leading to increased demand for homogeneous oligosaccharides. The stereoselective preparation of oligosaccharides by chemical means remains challenging and continues to be a vivid research area for organic chemists. In the past decade, new approaches and reinvestigated tradi-tional methods have transformed the field. These developments include novel catalyses, various types of glycosylation modulators and the use of photochemical energy to facilitate glycosylation. This Minireview presents a brief overview of the latest trends in chemical glycosylation, with emphasis on the stereoselective synthetic protocols developed in the past decade.[a] Dr.

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Recent advances in photoinduced glycosylation: oligosaccharides, glycoconjugates and their synthetic applications

Abstract: Carbohydrates have been demonstrated to perform imperative act in biological processes. This review highlights recent uses of photoinduced glycosylation in carbohydrate chemistry for the synthesis of oligosaccharides, thiosugars, glycoconjugates and glycoprotein.

Cited by 43 publications

References 152 publications

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

Stereoselective Synthesis of 2‐Deoxyglycosides from Glycals by Visible‐Light‐Induced Photoacid Catalysis

Synthesis of 1,3-divalent glycoconjugates with diverse structures and their functionalization

Recent Developments in Stereoselective Chemical Glycosylation

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