Chemistry and stereochemistry of internucleotide bond formation by the H-phosphonate method

Sobkowski, Michał

doi:10.1039/b9nj00679f

Cited by 8 publications

(1 citation statement)

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“…It has been reported that the stereoselectivity of the synthesis of oligonucleoside H-phosphonates can be significantly enhanced by the existence of a bulky substituent at the 2 0 -position. 54,55 This enhancement of stereoselectivity enables a stereoselective synthesis of P-chiral oligoribonucleotide analogs, although the same strategy is not applicable to 2 0 -deoxyribonucleotide analogs. For example, Stro¨mberg et al developed a method to synthesize diastereopure all-(Rp)-oligoribonucleoside phosphorothioates (PS-ORNs) via the H-phosphonate method (Scheme 2).…”

Section: Stereoselective Synthesis Of P-chiral Oligonucleotide Analog...mentioning

confidence: 99%

Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms

Oka

Wada

2011

Chem. Soc. Rev.

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Oligonucleotides, in which one of the two nonbridging oxygen atoms of internucleotidic phosphates is replaced by a different type of atom or a substituent, are useful as therapeutic agents and probes to elucidate mechanisms of enzymatic reactions. The internucleotidic phosphorus atoms of these oligonucleotides are chiral, and the properties of these oligonucleotides are affected by the absolute configuration of the chiral phosphorus atoms. In order to address the issue of chirality, various methods have been developed to synthesize these P-chiral oligonucleotide analogs in a stereocontrolled manner. This critical review focuses on the recent progress in this field (123 references).

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Section: Stereoselective Synthesis Of P-chiral Oligonucleotide Analog...mentioning

confidence: 99%

Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms

Oka

Wada

2011

Chem. Soc. Rev.

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ChemInform Abstract: Chemistry and Stereochemistry of Internucleotide Bond Formation by the H‐Phosphonate Method

Sobkowski

2010

ChemInform

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Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions

Sobkowski

Kraszewski

Stawiński

2014

Topics in Current Chemistry

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This review covers recent progress in the preparation of H-phosphonate mono- and diesters, basic studies on mechanistic and stereochemical aspects of this class of phosphorus compounds, and their fundamental chemistry in terms of transformation of P-H bonds into P-heteroatom bonds. Selected recent applications of H-phosphonate derivatives in basic organic phosphorus chemistry and in the synthesis of biologically important phosphorus compounds are also discussed.

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Chemistry and stereochemistry of internucleotide bond formation by the H-phosphonate method

Cited by 8 publications

References 100 publications

Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms

Stereocontrolled synthesis of oligonucleotide analogs containing chiral internucleotidic phosphorus atoms

ChemInform Abstract: Chemistry and Stereochemistry of Internucleotide Bond Formation by the H‐Phosphonate Method

Recent Advances in H-Phosphonate Chemistry. Part 1. H-Phosphonate Esters: Synthesis and Basic Reactions

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