Gold-catalysed glycosylation reaction using an easily accessible leaving group

Koppolu, Srinivasa Rao; Niddana, Ramana; Balamurugan, Rengarajan

doi:10.1039/c5ob00248f

Cited by 34 publications

(16 citation statements)

References 49 publications

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“…Glycosylations with catalysts like [Btz−Au−PPh 3 ]OTf and Ph 3 PAuOTf were seen to give the required product in excellent yields. Recently, Balamurugan and co‐workers introduced yet another easily accessible alkynyl leaving group, dipropargyl cyano acetate . per ‐Acetylated glycosyl analogs with this leaving group were optimized for glycosylation with various sugar acceptors and non‐sugar aglycons by varying both the solvent and catalyst systems.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

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Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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“…2,3,5,6‐Tetra‐ O ‐benzyl‐α‐D‐mannopyranosyl Azide (3d): The title com pound was prepared from 2,3,4,6‐tetra‐O‐benzyl‐methyl‐ α ‐D‐mannopyranoside. Purification by flash chromatography using 20 % ethyl acetate in hexanes afforded 3d (13.6 mg, 20 %) as a pale yellow oil.…”

Section: Methodsmentioning

confidence: 99%

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

2019

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Benzhydryl alcohols were converted into their corresponding diarylazidomethane analogues using azidotrimethylsilane (TMSN3) in the presence of a catalytic amount of a Brønsted acid HBF4·OEt2. The azidation reactions proceeded in high yields and demonstrated excellent functional group tolerance to electron‐donating and electron‐withdrawing substituents. In addition, a range of unprotected functional groups including amine, amide, aldehyde and alcohol were well‐tolerated. Furthermore, this methodology was successfully applied to carbohydrates for the preparation of the corresponding azide derivatives.

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“…In the course of a synthesis of carbocyclic lignan variants related to podophyllotoxin, a pseudo-anomeric stereospecific inversion of a carbasugar was achieved in good yield in Nishimura’s group [ 39 ]. More recently, the Mitsunobu procedure was applied in the context of gold-catalyzed glycosylation in order to install a reactive anomeric ester function in a series of O -benzylated glycoses ( 2 , 24 , 25 ) employing the branched carboxylic acid 26 ( Scheme 5 ) [ 40 ]. The produced esters 27 – 29 were obtained as anomeric mixtures.…”

Section: Reviewmentioning

confidence: 99%

Anomeric modification of carbohydrates using the Mitsunobu reaction

Hain¹,

Rollin²,

Klaffke³

et al. 2018

Beilstein J. Org. Chem.

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The Mitsunobu reaction basically consists in the conversion of an alcohol into an ester under inversion of configuration, employing a carboxylic acid and a pair of two auxiliary reagents, mostly triphenylphosphine and a dialkyl azodicarboxylate. This reaction has been frequently used in carbohydrate chemistry for the modification of sugar hydroxy groups. Modification at the anomeric position, leading mainly to anomeric esters or glycosides, is of particular importance in the glycosciences. Therefore, this review focuses on the use of the Mitsunobu reaction for modifications of sugar hemiacetals. Strikingly, unprotected sugars can often be converted regioselectively at the anomeric center, whereas in other cases, the other hydroxy groups in reducing sugars have to be protected to achieve good results in the Mitsunobu procedure. We have reviewed on the one hand the literature on anomeric esterification, including glycosyl phosphates, and on the other hand glycoside synthesis, including S- and N-glycosides. The mechanistic details of the Mitsunobu reaction are discussed as well as this is important to explain and predict the stereoselectivity of anomeric modifications under Mitsunobu conditions. Though the Mitsunobu reaction is often not the first choice for the anomeric modification of carbohydrates, this review shows the high value of the reaction in many different circumstances.

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Gold-catalysed glycosylation reaction using an easily accessible leaving group

Cited by 34 publications

References 49 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

A Direct Brønsted Acid‐Catalyzed Azidation of Benzhydrols and Carbohydrates

Anomeric modification of carbohydrates using the Mitsunobu reaction

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