Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

Mohamed, Bemba Sidi; Philouze, Christian; Mathé, Christophe

doi:10.3762/bjoc.13.28

Cited by 5 publications

(2 citation statements)

References 14 publications

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“…Purine coupling to carbohydrates and carbasugars through MR is regioselective for the N 9 position of the nucleobase, with only some rare examples of formation of N 7 -linked carbocyclic nucleosides as minor products, [70][71][72] and one report of N 3 coupling as a major product in isonucleoside synthesis, with both adenine and 8-azaadenine as pronucleophiles. 73 MR regioselectivity conducting to the N 9 linkage has also been found in acyclic nucleosides.…”

Section: 3-regioselectivity and Alkylation Of Purine Amino Groupsmentioning

confidence: 99%

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

Sousa¹,

Rauter²

2020

Arkivoc

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The coupling of a nucleobase is a key step in the synthesis of most nucleoside analogs, e.g. carbocyclic nucleosides, isonucleosides and acyclic nucleosides. The synthetic strategies for nucleosides based on Nglycosylation are not applied when the nucleobase is not linked to the anomeric center. Thus, other methods have been employed, mainly those based on the alkylation of nucleobases. The Mitsunobu reaction, in which a hydroxy group is replaced by a nucleophile, has also been extensively applied, generating a diversity of molecules, including pharmaceuticals and their precursors. In this review the usefulness of this reaction for the coupling of nucleobases to non-anomeric positions of sugars, carbasugars and other homocyclic and linear structures is highlighted and discussed, covering purines and pyrimidines as pronucleophiles.

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Section: 3-regioselectivity and Alkylation Of Purine Amino Groupsmentioning

confidence: 99%

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

Sousa¹,

Rauter²

2020

Arkivoc

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“…FA is a very vital pharmaceutical compound which finds use as a chemical intermediate compound such as for Vitamin C and Lysine production [92,93]. The latter being an essential amino acids not synthesised biologically in the human body [42].…”

Section: Pharmaceuticalsmentioning

confidence: 99%

Furfuryl Alcohol a Versatile, Eco-Sustainable Compound in Perspective

Iroegbu

Hlangothi

2018

Chemistry Africa

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Renewable agricultural biomass derived chemicals, their modifications and uses have seen multiplicity in numerous applications and important processes with major impacts on the pursuit for eco-sustainability. Such applications range include the energy sector, chemistry, pharmacy, the textile industry, paints and coatings, plastic industry, to name but a few. This field of lignocellulosic derived chemicals interconnects several scientific disciplines ranging from agriculture, biochemistry, engineering, environmental sciences, forestry, pharmacy, medicine, etc. hence making it difficult to have a single expert view on these complicated interactions. Therefore, the idea to create a focused review, specifically, on FA (an important furanic compound) is the main objective of this article. FA and its resultant derivatives exhibits an array of capabilities and fascinating properties in various fields of applications. As a compound or with co-reactants, it finds interesting applications as base and/or intermediate chemical compound, hypergolic rocket fuels, in flame resistant composites and coatings used in aerospace, auto, and the built environment; it also finds application as mortars, cementitious grouts, impregnating materials, and sealants due to its exceptional resistance to common corrosive chemicals such as acids, alkalis and other solvents when it is cross-linked. Coupled with its environmental and economic benefits FA has proved to be a remarkable eco-sustainable bio-derived compound.

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Recent advances in the synthesis of 4′-truncated nucleoside phosphonic acid analogues

Shen

Hong

2022

Carbohydrate Research

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Revaluation of biomass-derived furfuryl alcohol derivatives for the synthesis of carbocyclic nucleoside phosphonate analogues

Cited by 5 publications

References 14 publications

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

Nucleobase coupling by Mitsunobu reaction towards nucleoside analogs

Furfuryl Alcohol a Versatile, Eco-Sustainable Compound in Perspective

Recent advances in the synthesis of 4′-truncated nucleoside phosphonic acid analogues

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