Synthesis of divalent glycoamino acids with bis-triazole linkage

Sahoo, Laxminarayan; Singhamahapatra, Anadi; Kumar, K Muthu; Loganathan, Duraikkannu

doi:10.1016/j.carres.2013.08.006

Cited by 7 publications

(3 citation statements)

References 17 publications

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“…The methodology involved the click reaction of alkyne-functionalized divalent building blocks 74a−c with per-O-acetylated glycosyl azides or azidoacetamide to synthesize a diverse range of triazole-linked divalent glycoconjugates 75 (Scheme 26, Figure 9). 224 Likewise, Mukherjee et al synthesized C-spiro morpholinefused triazole-based glycoconjugates by modifying the C-spiro cyclopentenyl sugar. 225 The authors first carried out allylation of 2,3,4,6-tetra-O-benzyl-D-glucono-1,5-lactone (76) under Barbier conditions to afford the C,C-diallyl sugar using Zn powder, allyl bromide, and (TMS)Cl in a molar ratio of 6:4:0.3.…”

Section: Chemical Reviewsmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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Cu(I)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC), popularly known as the "click reaction", serves as the most potent and highly dependable tool for facile construction of simple to complex architectures at the molecular level. Click-knitted threads of two exclusively different molecular entities have created some really interesting structures for more than 15 years with a broad spectrum of applicability, including in the fascinating fields of synthetic chemistry, medicinal science, biochemistry, pharmacology, material science, and catalysis. The unique properties of the carbohydrate moiety and the advantages of highly chemo- and regioselective click chemistry, such as mild reaction conditions, efficient performance with a wide range of solvents, and compatibility with different functionalities, together produce miraculous neoglycoconjugates and neoglycopolymers with various synthetic, biological, and pharmaceutical applications. In this review we highlight the successful advancement of Cu(I)-catalyzed click chemistry in glycoscience and its applications as well as future scope in different streams of applied sciences.

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Section: Chemical Reviewsmentioning

confidence: 99%

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

et al. 2016

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“…In the literature, many diversely functionalized glycoconjugates are reported to be synthesized using a click reaction. [14][15][16] Recently, the synthesis of diversely functionalized "clickable" glycopeptoids 17 and other glycoconjugates, 18,19 such as triazole containing glycolipids, that are potentially useful in the area of chemical biology, were reported. In this present work, a series of novel difunctionalized glycoconjugate in which the sugar molecules were functionalized with azide or alkyne or both groups, which could be used for synthesis of complex glycoconjugates, was synthesized using Cu(I) catalyzed click reactions.…”

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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“…However, such methods have not been well developed. No doubt because of the propensity of nitronate anions to undergo alkylation at oxygen, S N 2 propargylations are limited to the use of nitroesters . Importantly, S N 2 propargylation of simple (less stabilized) nitroalkanes remains unknown (Figure a) .…”

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confidence: 99%

Copper-Catalyzed Propargylation of Nitroalkanes

et al. 2020

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Using a commercially available, inexpensive, and abundant copper catalyst system, an efficient α-functionalization of nitroalkanes with propargyl bromides is now established. This mild and robust method is highly functional group tolerant and provides straightforward access to complex secondary and tertiary homopropargylic nitroalkanes. Moreover, the utility of these α-propargylated nitroalkanes is demonstrated through downstream functionalization to biologically relevant, five-membered N-heterocycles such as pyrroles and 2-pyrrolines.

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Synthesis of divalent glycoamino acids with bis-triazole linkage

Cited by 7 publications

References 17 publications

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

Cu-Catalyzed Click Reaction in Carbohydrate Chemistry

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

Copper-Catalyzed Propargylation of Nitroalkanes

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