Protection of 5′‐Hydroxy Functions of Nucleosides

Seliger, H.

doi:10.1002/0471142700.nc0203s00

Cited by 9 publications

(10 citation statements)

References 211 publications

(272 reference statements)

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“…The conditions are stirring the substrate alcohol with trityl chloride in pyridine, which also serves as the base to neutralize the side product hydrogen chloride, at room temperature. 1 The method works well for unhindered primary alcohols. However, when it is used to protect the more hindered secondary alcohols, the reactions are usually slow and the yields are mostly poor.…”

Section: Introductionmentioning

confidence: 96%

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: Introductionmentioning

confidence: 96%

Tritylation of alcohols under mild conditions without using silver salts

Shahsavari

Chen

Wigstrom

et al. 2016

Tetrahedron Letters

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“…The original review on this topic was published in Current Protocols in Nucleic Acid Chemistry over two decades ago (Seliger, 2000). Therefore, it seems advisable to first summarize the key accomplishments in this field during the past 23 years.…”

Section: Overviewmentioning

confidence: 99%

“…Today, photolabile groups are extensively used because of their facile light‐triggered deprotection, spatio‐selective reaction, and overall speed necessary for the assembly of a nucleic acid library. The historical perspective is available in the original review (Seliger, 2000). During the past decade, new derivatives of the 2‐nitrophenylpropoxycarbonyl group (NPPOC) have been synthesized and evaluated to enhance photolytic efficiencies.…”

Section: Other 5′‐oh 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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“…One of the major challenges in converting functionalized nucleosides to oligonucleotide end products is the need for DMTr protection of the 5 -OH group. Yields of modification reactions are often low due to the moisture sensitivity of DMTr-Cl as well as the acid lability of the protected nucleoside (see Current Protocols article Seliger, 2001). Unfortunately, many modifications promoted by metal-mediated processes fail to make it to final application stages due to problems associated with DMTr protection.…”

Section: Introductionmentioning

confidence: 99%

Suzuki‐Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr‐Protected 5‐Iodo‐2′‐Deoxyuridine via Palladium‐catalyzed Reactions

Kori

Khandagale

Sanghvi³

et al. 2022

Current Protocols

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Modification of nucleosides via cross-coupling processes has been carried out extensively on unprotected halonucleosides to produce functionalized nucleosides that are often developed for incorporation into oligonucleotides or used as fluorescent probes. This approach requires protection of the 5 -OH with the 4,4 -dimethoxytrityl (DMTr) group, which is complicated and a common cause of reaction failure. Here we report a method for direct functionalization of 5 -O-DMTr-5-iodo-2 -deoxyuridine via Suzuki-Miyaura cross-coupling, Heck alkenylation, and carboamidation. This approach facilitates rapid synthesis of a variety of C5-substituted 5 -O-DMTr-2 -deoxyuridine derivatives. © 2022 Wiley Periodicals LLC. BasicProtocol 1: Synthesis of the SerrKap palladacycle complex Basic Protocol 2: Suzuki-Miyaura coupling of 5 -O-DMTr-5-iodo-2deoxyuridine using SerrKap palladacycle Basic Protocol 3: Heck coupling of 5 -O-DMTr-5-iodo-2 -deoxyuridine using SerrKap palladacycle Basic Protocol 4: Heck coupling of 5 -O-DMTr-5-iodo-2 -deoxyuridine with Ruth linker using Pd(OAc) 2 /PTABS Basic Protocol 5: Carbonylative amidation of 5 -O-DMTr-5-iodo-2deoxyuridine using Pd(OAc) 2 /PTABS

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Protection of 5′‐Hydroxy Functions of Nucleosides

Cited by 9 publications

References 211 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

Suzuki‐Miyaura Coupling, Heck Alkenylation, and Amidation of DMTr‐Protected 5‐Iodo‐2′‐Deoxyuridine via Palladium‐catalyzed Reactions

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