Biocatalytic route to <i>C</i>-4′-spiro-oxetano-xylofuranosyl pyrimidine nucleosides

Rungta, Pallavi; Mangla, Priyanka; Khatri, Vinod; Maity, Jyotirmoy; Prasad, Ashok K.

doi:10.1080/10242422.2018.1438416

Cited by 4 publications

(2 citation statements)

References 31 publications

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“…However, we started with the low cost commercially available starting material, diacetone glucofuranose and successfully protected 3′‐hydroxy group of diacetonide with 2‐bromomethylnaphthalene to provide 3‐ O ‐(2‐naphthylmethyl)‐1,2:5,6‐di‐ O ‐isopropylidene‐ α ‐D‐glucofuranose ( 1 ) in quantitative yield . Further, compound 1 was partially hydrolysed with 80% AcOH‐H 2 O to afford 3‐ O ‐(2‐naphthylmethyl)‐1,2‐ O ‐isopropylidene‐ α ‐D‐glucofuranose, which on oxidative cleavage with sodium periodate in dioxane‐water followed by Aldol‐Cannizzaro reaction resulted in the formation of dihydroxy furanose 2 in 80% overall yield, over three steps (Scheme ) ,…”

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confidence: 99%

Synthesis of 6′‐Methyl‐2′‐O,4′‐C‐methylene‐α‐L‐ ribofuranosyl‐pyrimidine Nucleosides

et al. 2019

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Herein, we report the efficient synthesis of (6′R)‐ and (6′S)‐6′‐methyl‐2′‐O,4′‐C‐methylene‐α‐L‐ribofuranosyl‐thymine, and (6′R)‐ and (6′S)‐6′‐methyl‐2′‐O,4′‐C‐methylene‐α‐L‐ribofuranosyl‐uracil starting from diacetone glucofuranose in overall yields of 6.3, 4.7, 5.4 and 4.0%, respectively. The key step in the synthesis of stereochemically defined 6′‐Me‐bicyclic‐nucleosides is the nucleophilic addition of methyl group at methylene carbon of 4‐C–CH2OH moiety of the 4‐C‐tert‐butyldiphenylsilyloxymethylated sugar precursor. Thus, the methyl group was added on the aldehyde obtained from Dess‐Martin periodinane oxidation of the precursor alcohol employing AlMe3 in hexane. Both (6′R)‐ and (6′S)‐stereoisomers of bicyclic nucleosides T and U were successfully synthesized following Vorbrüggen nucleobase coupling of T and U with triacetylated glycosyl donor obtained from acetolysis of (5R)‐ and (5 S)‐4‐C‐(tert‐butyldiphenylsilyloxymethyl)‐5‐C‐methyl‐1,2‐O‐isopropylidene‐3‐O‐(2‐naphthylmethyl)‐α‐D‐xylofuranoses and further cyclization and deprotection of the resulted nucleoside. One of the nucleosides, (6′R)‐6′‐methyl‐2′‐O,4′‐C‐methylene‐α‐L‐ribofuranosyl‐uracil has been reported earlier in 1.8% yield, while the present methodology yielded the nucleoside in 5.4% yield. All the synthesized 6′‐Me‐bicyclic‐nucleosides showed no significant anti‐viral activity against H1 N1 strain of influenza A virus (A/Puerto Rico/8/1934).

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Section: Resultsmentioning

confidence: 99%

Synthesis of 6′‐Methyl‐2′‐O,4′‐C‐methylene‐α‐L‐ ribofuranosyl‐pyrimidine Nucleosides

et al. 2019

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“…77 The Prasad group reported an enzyme-mediated synthesis of C-4′-spirocyclic-oxetano-xylofuranosyl nucleosides T and U (Scheme 60). 78 The precursor diol 405a,b was obtained from 402 in three steps consisting of acetolysis to 403a,b, Vorbrüggen nucleobase coupling with T and U to 404a,b, and treatment with methanolic ammonia resulted in deacetylation to afford 405a,b. The lipase, Lipozyme ® TL IM in MeCN was found to be most selective for the conversion of 405a,b into 406a,b in high yields.…”

Section: Short Review Synthesismentioning

confidence: 99%

Advances in the Synthesis of Spirocyclic Nucleosides

Kumar,

Khan,

Arora

et al. 2023

Synthesis

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The nucleosides are the building blocks for nucleic acids and composed of a five-carbon sugar bearing either pyrimidine or purine nucleobase. The biological properties of nucleosides can be tailored by chemically modifying the five-carbon sugar to influence its sugar pucker. The spirocyclic scaffold is an indispensable scaffold in more than ten approved drugs, and its inherent three-dimensionality makes it an ideal modification to influence the sugar pucker and biological properties of nucleosides. However, the introduction of spirocyclic scaffold is often synthetically challenging due to increase in synthetic steps and stereocenters. The present review highlights the advances in synthetic methodologies developed during the past decades for accessing various members of the spiro-functionalized nucleoside family.1 Introduction2 C-1′-Spirocyclic Nucleosides3 C-2′-Spirocyclic Nucleosides4 C-3′-Spirocyclic Nucleosides5 C-4′-Spirocyclic Nucleosides6 Miscellaneous Spirocyclic Nucleosides7 Conclusion and Future Perspectives

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