Synthesis of Some 2′,3′-Dideoxy-3′-C-Fluoromethyl and 3′-C-Azidomethyl Nucleosides

Svansson, Lars; Kvarnström, Ingemar; Classon, Björn; Samuelsson, Bertil

doi:10.1080/07328319208021178

Cited by 10 publications

(2 citation statements)

References 18 publications

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“…To synthesize 3‘- C -azidomethyl-2‘,3‘-dideoxynucleosides, the 3‘- C -hydroxymethyl furanoside 7.027 was converted to the corresponding 3‘- C -azidomethyl furanoside 7.028 using Ph 3 P−CBr 4 - LiN 3 . Silylated purine and pyrimidine bases were subsequently glycosylated with 7.029 obtained from 7.028 to afford, after deprotection, nucleosides 7.030 − 7.032 along with the corresponding α-anomers …”

Section: 2 2‘(3‘)-c-azidomethyl-2‘(3‘)-deoxynucleosidesmentioning

confidence: 99%

Azidonucleosides: Synthesis, Reactions, and Biological Properties

Pathak

2002

Chem. Rev.

156

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Section: 2 2‘(3‘)-c-azidomethyl-2‘(3‘)-deoxynucleosidesmentioning

confidence: 99%

Azidonucleosides: Synthesis, Reactions, and Biological Properties

Pathak

2002

Chem. Rev.

156

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“…Although the nucleotide has a somewhat higher affinity for the enzyme, the parent nucleoside exhibits affinity for bacterial TMPKT in the same order of magnitude and displays a superior selectivity profile versus human TMPKT. However, both purine and pyrimidine nucleosides based on the 3 0 -fluoromethylriboside unit in 2 do not exhibit antiviral activity [14,15]. These and other nucleosides are prepared by classical approaches involving lengthy multi-step sequences starting from sugar precursors.…”

Section: Introductionmentioning

confidence: 98%

Synthesis of fluorocyclobutanones and their use in the synthesis of fluoronucleosides

Ghazi

Lee‐Ruff

2005

Journal of Fluorine Chemistry

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Synthesis Of Nucleosides

Vorbrüggen¹,

1999

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This chapter deals with the synthesis of nucleosides (e.g., the formation of N ‐glycosides of sugars such as D ‐ribose or 2‐deoxy‐D‐ribose with heterocyclic nitrogen bases). The methods of nucleoside synthesis have been treated in a number of reviews and monographs. It is now generally accepted that nucleosides were among the first organic compounds formed at the start of evolution in the early history of our planet earth. To support this point, guanine and adenine were heated with D ‐ribose in seawater, which contains the Lewis acid magnesium chloride as catalyst. One thus obtained the nucleosides guanosine and adenosine together with comparable yields of unnatural α‐nucleosides. The latter were gradually photoanomerized to the thermodynamically more stable compounds in overall yields of 5–6%. The furanose form of ribose reacts faster than the pyranose form. Corresponding syntheses of the pyrimidine nucleosides uridine and cytidine from uracil , cytosine and ribose are more problematic and remain an enigma. The recent conversion of glycolaldehyde‐ O ‐phosphate and formaldehyde to ribose‐2,4‐di‐ O ‐phosphate might give new insights into the prebiotic syntheses of uridine and cytidine. The evidence and hypotheses for these prebiotic conversions and the evolution of RNA, as well as the implications of an “RNA World,” have been reviewed. These RNA nucleosides are reduced in vivo as 5′‐ O ‐diphosphates by ribonucleotide reductases to the corresponding 2′‐deoxynucleosides—the building blocks of DNA such as 2′‐deoxyguanosine. The thermodynamically controlled synthesis of these four building blocks of RNA has implications for the design of efficient, high yielding, new methods for the synthesis of the naturally occurring nucleosides, nucleoside antibiotics, and modified nucleosides that may serve as antimetabolites to fight viral and parasitic diseases and cancer. The nucleoside rings in this chapter are depicted arbitrarily in the anti conformation, as occurs predominantly in the crystal and solution (based primarily on NOE‐ 1 H‐ and 13 C‐NMR measurements) forms of pyrimidine nucleosides. Only a few nucleosides, such as 6‐methyluridine, occur with the heterocyclic ring predominantly in the syn conformation. The synthesis of C ‐nucleosides has been reviewed previously and is not covered in this review.

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Synthesis of Some 2′,3′-Dideoxy-3′-C-Fluoromethyl and 3′-C-Azidomethyl Nucleosides

Cited by 10 publications

References 18 publications

Azidonucleosides: Synthesis, Reactions, and Biological Properties

Azidonucleosides: Synthesis, Reactions, and Biological Properties

Synthesis of fluorocyclobutanones and their use in the synthesis of fluoronucleosides

Synthesis Of Nucleosides

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