1620086-77-2

Basic information

• Product Name: 5-chloro-saligenyl-N,N-diisopropylphosphoramidite
• CAS NO: 1620086-77-2
• Molecular Weight: 287.726
• Mol File: 1620086-77-2.mol
• Article Data: 3

Chemical Properties

• Melting Point: 45 °C
• Boiling Point: 341.4±52.0 °C(Predicted)
• CAS DataBase Reference: 5-chloro-saligenyl-N,N-diisopropylphosphoramidite(CAS DataBase Reference)
• NIST Chemistry Reference: 5-chloro-saligenyl-N,N-diisopropylphosphoramidite(1620086-77-2)
• EPA Substance Registry System: 5-chloro-saligenyl-N,N-diisopropylphosphoramidite(1620086-77-2)

Safety Data

• Hazardous Substances Data: 1620086-77-2(Hazardous Substances Data)

Usage

Description

5-Chlorosaligenyl-N,N-diisopropylphosphoramidite is an organic compound that serves as a key reagent in the synthesis of various biologically active molecules, particularly in the field of nucleoside chemistry. It is characterized by its ability to form stable phosphite intermediates, which are crucial for the construction of complex phosphate-bridged nucleoside conjugates.

Uses

Used in Pharmaceutical Industry:
5-Chlorosaligenyl-N,N-diisopropylphosphoramidite is used as a synthetic reagent for the solid-phase synthesis of phosphate-bridged nucleoside conjugates. Its application is significant in the development of novel therapeutic agents, particularly in the treatment of viral infections and certain genetic disorders. The reagent enables the formation of stable phosphite intermediates, which are essential for the synthesis of these complex molecules, ultimately leading to the production of potential pharmaceutical candidates with improved efficacy and selectivity.
Used in Chemical Research:
In the field of chemical research, 5-chlorosaligenyl-N,N-diisopropylphosphoramidite is utilized as a valuable tool for the synthesis of various phosphorus-containing compounds. Its unique reactivity and stability make it an attractive choice for the development of new methodologies and the exploration of novel chemical reactions involving phosphorus centers. This contributes to the advancement of knowledge in organic chemistry and the discovery of new applications for phosphorus compounds in various industries.

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Relevant articles and documents

Efficient Automated Solid-Phase Synthesis of DNA and RNA 5′-Triphosphates

A fast, high-yielding and reliable method for the synthesis of DNA- and RNA 5′-triphosphates is reported. After synthesizing DNA or RNA oligonucleotides by automated oligonucleotide synthesis, 5-chloro-saligenyl-N,N-diisopropylphosphoramidite was coupled to the 5′-end. Oxidation of the formed 5′-phosphite using the same oxidizing reagent used in standard oligonucleotide synthesis led to 5′-cycloSal-oligonucleotides. Reaction of the support-bonded 5′-cycloSal-oligonucleotide with pyrophosphate yielded the corresponding 5′-triphosphates. The 5′-triphosphorylated DNA and RNA oligonucleotides were obtained after cleavage from the support in high purity and excellent yields. The whole reaction sequence was adapted to be used on a standard oligonucleotide synthesizer.

Operationally simple regioselective 59-phosphorylation of unprotected 5-ethynyl-29-deoxyuridine analogues

Here, we present the development of a straightforward methodology to regioselectively phosphorylate the 50-OH group of unprotected nucleosides. We employ cyclosaligenyl phosphoramidite reagents together with pyridinium trifluoroacetate as activator, followed by in situ oxidation to prepare a panel of novel nucleoside-based chemical probes, ProLabel compounds 4-15. Alternative procedures for this transformation are available, but are limited in number and scope. Furthermore, the benefits of the new methodology include milder reaction conditions, wider solvent applicability, and, by avoiding sensitive reagents, a more straightforward handling of reagents, reactions, and workup processes. The panel of novel cyclosaligenyl phosphotriester uridine ProLabels have variable 20 substituents (H, F, Cl, Br, I) as well as four different cyclosaligenyl groups that would span a range of half-lives for in vitro applications.