Advances in Pd-catalyzed C–C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules

Hussain, Nazar; Hussain, Altaf

doi:10.1039/d1ra06351k

Cited by 21 publications

(6 citation statements)

References 142 publications

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“…Herein, we will discuss the applications of the two main classes: 1) conjugated 1,3-dienes (Section 2.1); and 2) non-conjugated 1,6dienes (Section 2.2). A number of different strategies have been described to prepare carbohydrate-based dienes, such as Wittig olefination of α-carbonylfunctionalized glycals, [19] enyne metathesis, [20][21][22] coupling reactions [23] and elimination reactions, [24] and will not be described further within the scope of this review.…”

Section: Carbohydrate-based Dienesmentioning

confidence: 99%

Carbohydrate‐Derived Dienes as Building Blocks for Pharmaceutically Relevant Molecules

Dubbu

Santhi

Hevey

2022

Helvetica Chimica Acta

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Carbohydrate‐based dienes are valuable building blocks for a variety of highly functionalized carbo‐ and oxa‐cycles by virtue of their high degree of inherent stereochemical information, and suitability in various synthetic transformations. Research into the chemistry of carbohydrate‐based dienes has been expanding over the last decades due to its unique applications in the construction of diverse and complex structural frameworks. In this review, we describe the main transformations of this interesting class of molecule and highlight their utility in the construction of diverse ring systems important for drug development.

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Section: Carbohydrate-based Dienesmentioning

confidence: 99%

Carbohydrate‐Derived Dienes as Building Blocks for Pharmaceutically Relevant Molecules

Dubbu

Santhi

Hevey

2022

Helvetica Chimica Acta

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“…Nevertheless, there is a mighty tool of organic synthesis that has not been enough explored as a route to glycoporphyrins. These are metal‐catalysed reactions, a strategy widely used for both subunits: pophyrin derivatives [32–34] and in sugar chemistry [35,36] …”

Section: Introductionmentioning

confidence: 99%

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Godlewski,

Malinowski

2024

Adv Synth Catal

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Glycoporphyrins are considered promising photosensitisers of new generation. Herein, we describe the original, metal‐catalysed method towards porphyrin‐carbohydrate C‐C conjugates. The protocol of Suzuki‐Miyaura reaction has been developed and it was compatible with peracetylated 2‐iodoglycals. The utility of the reaction was exemplified on 15 different (C‐2)‐arylated sugar derivatives. Then it was applied on more challenging starting materials, namely, porphyrin boronates in which we addressed the issues of difficult transmetalation step usually observed on palladium‐catalysed processes of porphyrin derivatives. The efficiency of the protocol was finally applied to synthesize the library of glycoporphyrins proving the versatile character of this strategy. Keywords: Suzuki‐Miyaura reaction, glycoporphyrins, photosensitisers, carbohydrates, porphyrins, palladium catalysis, glycal

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“…47 In 2021, Hussain and Hussain broadly reviewed the recent progress on the Pd-catalyzed synthesis of C-glycosides and branched sugars. 48 Meanwhile, in 2020, Ye et al reviewed the synthesis of C-glycosides from glycals achieved prior to 2010. 49 The present short review aims to…”

Section: Introductionmentioning

confidence: 99%

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

Mukherjee,

Kundu,

Das

et al. 2023

Synthesis

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The development of stereoselective synthetic routes for C-glycosides has attracted immense attention from carbohydrate chemists in the last two decades. In this review, progress made in the last decade towards the synthesis of C-glycosides using glycals as a precursor are discussed. Glycals have been extensively manipulated to generate oxocarbenium cation or glycosyl anion to form C-C bond at the anomeric position through attack with C-nucleophiles or transition metal catalyzed coupling reactions. Recent reports on carbon Ferrier, intramolecular Cope, Claisen rearrangements, various coupling reactions in the presence or absence of directing groups are deliberated herein. Contemporary applications of these reactions in the syntheses of natural products, drugs and scaffolds with bioactive potential are briefly discussed.

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Advances in Pd-catalyzed C–C bond formation in carbohydrates and their applications in the synthesis of natural products and medicinally relevant molecules

Abstract: This review highlights the recent progress of Pd-catalyzed reactions in carbohydrates. Different types strategies and applications in the synthesis of natural products, SGLT2 inhibitors and biologically active have been included in this review.

Cited by 21 publications

References 142 publications

Carbohydrate‐Derived Dienes as Building Blocks for Pharmaceutically Relevant Molecules

Carbohydrate‐Derived Dienes as Building Blocks for Pharmaceutically Relevant Molecules

Suzuki‐Miyaura Reaction of Glycals with Base‐Labile Protecting Groups as a New Route to Glycoporphyrins

Recent Advances on the Synthesis of C-Glycosides from 1,2-Glycals

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