&lt;b&gt;A solvent free and selective method for preparation of triphenylmethyl ethers of alcohols and nucleosides&lt;/b&gt;

Zekri, Negar; Alamdari, Reza Fareghi; Khalafi‐Nezhad, Ali

doi:10.4314/bcse.v24i2.54764

Cited by 8 publications

(5 citation statements)

References 16 publications

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“…However, microwave irradiation had been used to facilitate the reactions. 8 Compound 8b was also made using benzyl dimethoxytrityl ether as the reagent in good yield, but expensive reagents including diethyl azodicarboxylate and Ce(OTf) 4 had to be used as activators. 9 Compared to those reported methods for tritylation of secondary alcohols, our method is much simpler and uses much less expensive reagents.…”

Section: Resultsmentioning

confidence: 99%

Tritylation of alcohols under mild conditions without using silver salts

Shahsavari

Chen

Wigstrom

et al. 2016

Tetrahedron Letters

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Secondary alcohols were conveniently tritylated under mild conditions within a short running time with tritylium trifluoroacetate generated in situ from trityl alcohols and trifluoroacetic anhydride. No expensive silver salts were needed for the reactions. Four secondary alcohols were tritylated with both mono- and dimethoxy trityl alcohols giving good to excellent isolated yields. The reaction was also tested on four nucleoside derivatives that have primary alcohols. Satisfactory results were also obtained.

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Section: Resultsmentioning

confidence: 99%

Tritylation of alcohols under mild conditions without using silver salts

Shahsavari

Chen

Wigstrom

et al. 2016

Tetrahedron Letters

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“…The 5′‐hydroxyl group of a nucleoside is conventionally reacted with 4,4′‐dimethoxytrityl chloride (DMTr‐Cl) in pyridine in the presence of 4‐dimethylaminopyridine to introduce the DMTr group with high selectivity and excellent yield. Use of solvents can be avoided if the nucleoside is reacted with DMTr‐Cl and triethylamine under microwave irradiation (Zekri & Alamdari, 2010; Zekri, Alamdari & Khalafi‐Nezhad, 2010). More recently, DMTr protection has been accomplished on an industrial kilogram scale using 2,6‐lutidine as a base (McPherson et al., 2020).…”

Section: Trityl and Related Protecting Groupsmentioning

confidence: 99%

An Update on Protection of 5′‐Hydroxyl Functions of Nucleosides and Oligonucleotides

Seliger,

Sanghvi

2024

Current Protocols

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The synthesis of natural and chemically modified nucleosides and oligonucleotides is in great demand due to its increasing number of applications in diverse areas of research. These include tools for diagnostics and proteomics, research reagents for molecular biology, probes for functional genomics, and the design, discovery, development, and manufacture of new therapeutics. The likelihood of success in synthesizing these molecules is often dependent on the correct choice of a protection strategy to block the 5′‐hydroxyl group of a carbohydrate moiety, nucleoside, or oligonucleotide. This topic was reviewed extensively in the year 2000. The purpose of this article is to complement and update the original review with recently published methodologies recommended for the protection and deprotection of the 5′‐hydroxyl group. © 2024 Wiley Periodicals LLC.

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“…An attempt to protect the 5'-hydroxyl function in 5-ethynyl-2'-deoxycytidine (8) with a trityl group using DMTrCl in pyridine containing triethylamine or in triethylamine only used as a solvent, under microwave irradiation, 30 failed. Synthesis of 2'-deoxyguanosine derivative 16 with a propargyl group at O-6 position and a dmf group at exocyclic amino function was achieved by a simple stirring of 16 with N,N-dimethylformamidine dimethyl acetal and methanol.…”

Section: Figmentioning

confidence: 99%

Nucleoside bearing boron clusters and their phosphoramidites – building blocks for modified oligonucleotide synthesis

et al. 2015

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This paper describes a general method for the synthesis of four canonical nucleosides T, dC, dA and dG and their phosphoramidites suitable for automated synthesis of DNA modified with a carborane cage. A boron cluster in the form of an electroneutral, lipophilic 1,2-dicarba-closododecaborane (C2B9H11) or negatively charged, redox-active 7,8-dicarba-nido-undecaborate ion (C2B9H12(-1)) was used as a modifying unit. The method is based on the "click chemistry" type Huisgen-Sharpless-Meldal reaction. All boron cluster-nucleoside conjugates have been characterized electrochemically, they have shown different redox potentials allowing for selective electrochemical identification of individual nucleosides in the mixture. There is also the first description of the crystallographic structure of the boron cluster-nucleoside conjugate: N 3 -{[(ocarboran-1-yl)propyl]-1N-1,2,3-triazol-4-yl}methylenethymidine.

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<b>A solvent free and selective method for preparation of triphenylmethyl ethers of alcohols and nucleosides</b>

Cited by 8 publications

References 16 publications

Tritylation of alcohols under mild conditions without using silver salts

Tritylation of alcohols under mild conditions without using silver salts

An Update on Protection of 5′‐Hydroxyl Functions of Nucleosides and Oligonucleotides

Nucleoside bearing boron clusters and their phosphoramidites – building blocks for modified oligonucleotide synthesis

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