2021
DOI: 10.1039/d0nj03253k
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Chemo-enzymatic access toC-4′-hydroxyl-tetrahydrofurano-spironucleosides

Abstract: The biocatalytic synthesis of C-4′-hydroxyl-tetrahydrofurano-spironucleosides where the tetrahydrofuranospirocyclic ring at C-4′ position locks the furanose ring of nucleosides in the NE-conformation (C4′-exo).

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Cited by 2 publications
(3 citation statements)
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“…Several nucleoside derivatives adopting a favored C 4′- exo conformations have already been reported in the literature. In all cases, these derivatives are constrained either by chemical modifications of the sugar, 62–64 or because of an association of a nucleotide with a protein target. 65…”
Section: Resultsmentioning
confidence: 99%
See 1 more Smart Citation
“…Several nucleoside derivatives adopting a favored C 4′- exo conformations have already been reported in the literature. In all cases, these derivatives are constrained either by chemical modifications of the sugar, 62–64 or because of an association of a nucleotide with a protein target. 65…”
Section: Resultsmentioning
confidence: 99%
“…Several nucleoside derivatives adopting a favored C 4′-exo conformations have already been reported in the literature. In all cases, these derivatives are constrained either by chemical modifications of the sugar, [62][63][64] or because of an association of a nucleotide with a protein target. 65 The 6′-boronic acid uridine analogue 3 described here is an example of a highly constrained structure, due to both the formation of a five-membered-ring at the 2′-3′ extremities of the sugar and the head-to-tail cyclization.…”
Section: Organic and Biomolecular Chemistry Papermentioning
confidence: 99%
“…The Prasad group reported a methodology for the chemoenzymatic synthesis of C -4′-hydroxy-tetrahydrofuranose. 79 The synthetic procedure involved the use of lipase, Lipozyme ® TL IM for the selective protection of the hydroxy group in 410 , obtained from d -glucose, to access 411a (Scheme 61 ). The monoacylated compound 411a was used to synthesize tetraacetylated glycosyl donor 415a , b .…”
Section: -4′-spirocyclic Nucleosidesmentioning
confidence: 99%