Synthesis of 3′-deoxy-3′-C-methyl nucleoside derivatives

Aljarah, Mohamed; Couturier, Sarah; Mathé, Christophe; Philouze, Christian

doi:10.1016/j.bmc.2008.06.011

Cited by 9 publications

(5 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…In the initial step, inosine was O ‐acylated for selective MEM group introduction and then deacylated with NH 3 /MeOH prior to ring opening for better solubility in water. Similarly, the acid labile 5‐ O ‐trityl‐ 45 b , [36] 3‐deoxy‐3‐ C ‐methyl‐ 45 c , [42] 5‐azido‐5‐deoxy‐2,3‐ O ‐isopropylidene‐ 45 d [43] protected inosines and arabinosyl hypoxanthine ( 45 e ) [44] – could be transformed to AICAR analogues. The Yamamoto group also demonstrated a synthesis of 2‐aryl‐AICARs 45 f – l .…”

Section: Ring Opening Of the Pyrimidine Moiety In Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

View full text Add to dashboard Cite

Purines, which are regarded as relatively stable heterocyclic systems, can be opened at both pyrimidine and imidazole rings. Purine ring opening also serves as a tool for the preparation of ring-modified purines through rearrangement/recyclization mechanisms. The obtained imidazole, pyrimidine, and purine derivatives are privileged molecular scaffolds in medicinal and agricultural chemistry. Purine ring-opening approach is a useful alternative for their synthesis, which competes well with de novo approach or modification of a conserved heterocyclic core. The substitution patterns and groups that activate purines towards ring opening are reviewed. Moreover, mechanistic studies using labelled substrates, which are leading to rearranged purine derivatives are covered. Furthermore, an insight into imidazole ring opening upon exposure of purine system to DNA damaging agents is provided.

show abstract

Section: Ring Opening Of the Pyrimidine Moiety In Purinesmentioning

confidence: 99%

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

et al. 2021

View full text Add to dashboard Cite

show abstract

“…A key goal within the field of late-stage functionalization is to access multiple structural analogs from a single complex molecule ( 33 ). Historically, the installation of small alkyl groups at the 3′ position of nucleosides has posed a substantial challenge, requiring that each analog be synthesized independently in a lengthy multistep sequence ( 47 ). We sought to circumvent this barrier by using our cross-alcohol coupling protocol to rapidly synthesize a small library of 3′-functionalized nucleosides.…”

Section: Evaluation Of Methanol Coupling Scopementioning

confidence: 99%

Alcohol-alcohol cross-coupling enabled by S _H 2 radical sorting

Chen,

Intermaggio,

Xie

et al. 2024

Science

View full text Add to dashboard Cite

Alcohols represent a functional group class with unparalleled abundance and structural diversity. In an era of chemical synthesis that prioritizes reducing time to target and maximizing exploration of chemical space, harnessing these building blocks for carbon-carbon bond-forming reactions is a key goal in organic chemistry. In particular, leveraging a single activation mode to form a new C(sp 3 )–C(sp 3 ) bond from two alcohol subunits would enable access to an extraordinary level of structural diversity. In this work, we report a nickel radical sorting–mediated cross-alcohol coupling wherein two alcohol fragments are deoxygenated and coupled in one reaction vessel, open to air.

show abstract

“…Nucleosides analogs are widely used as antiviral and anticancer drugs, since they can act as inhibitors of viral or cellular DNA replication [1][2][3][4][5]. In particular, thymidine is a useful precursor in the chemical synthesis of various antiviral drugs including stavudine and zidovudine, active ingredients in formulations for the treatment of AIDS [6].…”

Section: Introductionmentioning

confidence: 99%

Selection of a New Whole Cell Biocatalyst for the Synthesis of 2-Deoxyribose 5-Phosphate

Valino

Palazzolo

Iribarren

et al. 2011

Appl Biochem Biotechnol

View full text Add to dashboard Cite

2-deoxyribose 5-phosphate (DR5P) is a key intermediate in the biocatalyzed preparation of deoxyribonucleosides. Therefore, DR5P production by means of simpler, cleaner, and economic pathways becomes highly interesting. One strategy involves the use of bacterial whole cells containing DR5P aldolase as biocatalyst for the aldol addition between acetaldehyde and D: -glyceraldehyde 3-phosphate or glycolytic intermediates that in situ generate the acceptor substrate. In this work, diverse microorganisms capable of synthesizing DR5P were selected by screening several bacteria genera. In particular, Erwinia carotovora ATCC 33260 was identified as a new biocatalyst that afforded 14.1-mM DR5P starting from a cheap raw material like glucose.

show abstract

Synthesis of 3′-deoxy-3′-C-methyl nucleoside derivatives

Cited by 9 publications

References 13 publications

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Alcohol-alcohol cross-coupling enabled by S _H 2 radical sorting

Selection of a New Whole Cell Biocatalyst for the Synthesis of 2-Deoxyribose 5-Phosphate

Contact Info

Product

Resources

About

Synthesis of 3′-deoxy-3′-C-methyl nucleoside derivatives

Cited by 9 publications

References 13 publications

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Applications of Purine Ring Opening in the Synthesis of Imidazole, Pyrimidine, and New Purine Derivatives

Alcohol-alcohol cross-coupling enabled by S H 2 radical sorting

Selection of a New Whole Cell Biocatalyst for the Synthesis of 2-Deoxyribose 5-Phosphate

Contact Info

Product

Resources

About

Alcohol-alcohol cross-coupling enabled by S _H 2 radical sorting