A Simple and Efficient Synthesis of 2-Deoxy-<scp>l</scp>-ribose from 2-Deoxy-<scp>d</scp>-ribose

A straightforward method for the conversion of a low-cost carbohydrate (d-fructose) into an important carbohydrate building block (2-deoxy-l-ribose) is reported. This methodology involves a novel radical cyclization followed by a fragmentation reaction, selective enzymatic hydrolysis using a lipase, and oxidative cleavage of the vicinal diol. This method uses the cheapest starting material and employs the shortest synthetic route (7 steps) for converting a d-sugar into 2-deoxy-l-ribose.

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Synthesis of l-Deoxyribonucleosides from d-Ribose

Song

Liu

Chang

2018

J. Org. Chem.

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The preparation of 2-deoxy-l-ribose derivatives or mirror image deoxyribonucleosides (l-deoxyribonucleosides) from d-ribose is reported. Starting from inexpensive d-ribose, an acyclic d-form carbohydrate precursor was synthesized to study a unique carbonyl translocation process. In this novel radical reaction, not only was the configuration of the sugar transformed from the d-form to the l-form, but also deoxygenation at the C(2) position of the sugar was successfully achieved. This is one of the most practical methods for converting a d-sugar to a 2-deoxy-l-sugar in a one-step reaction. To further identify the reaction product, radical reactions followed by treatment with 1,3-propanedithiol and then benzoylation were performed to afford a dithioacetal derivative. The stereochemistry and configuration of the 2-deoxy-l-ribose dithioacetal derivative were confirmed by its X-ray crystal structure. To further apply this methodology, a diethyl thioacetal derivative was formed, followed by selective benzoyl protection, and an NIS-initiated cyclization reaction to give the desired ethyl S-l-2-deoxyriboside, which can be used as a 2-deoxy-l-ribosyl synthon in the formal total synthesis of various l-deoxyribonucleosides, such as l-dT.

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A Simple and Efficient Synthesis of 2-Deoxy-l-ribose from 2-Deoxy-d-ribose

Cited by 3 publications

References 3 publications

Addition of mirror-image L-DNA elements to DNA amplification circuits to distinguish leakage from target signal

Addition of mirror-image L-DNA elements to DNA amplification circuits to distinguish leakage from target signal

From a Carbohydrate Raw Material to an Important Building Block: Cost-Efficient Conversion of d-Fructose into 2-Deoxy-l-ribose

Synthesis of l-Deoxyribonucleosides from d-Ribose

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