Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

Punzo, Francesco; Cowley, Andrew R.; Watkin, David J.; Simone, Michela I.; Edwards, Alison A.; Tranter, George E.; Fleet, George W. J.

doi:10.1107/s1600536805043205

Cited by 3 publications

(2 citation statements)

References 16 publications

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“…For the synthesis of the title compound, see: Simone et al (2008Simone et al ( , 2010. For structures related to the title molecule, and their characteristic features, see: Punzo et al (2006); Humphreys et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

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Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

et al. 2010

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The title compound, C22H25F5N4O9, is a stable pentafluorophenyl ester intermediate in the synthesis of novel homo-oligomeric structures containing branched carbon chains. The structure is epimeric to the previously characterized dimeric pentafluorophenyl ester with stereochemistry (3R,4R,5R), which was synthesized using d-ribose as starting material. The crystal structure of the title molecule removes any ambiguities arising from the relative stereochemistries of the six chiral centres. Two hydrogen bonds, bifurcating from the NH group, stabilize the crystal: one intramolecular and one intermolecular, both involving O atoms of the methoxy groups. The asymmetric unit contains two independent molecules not related by any pseudo-symmetry operators. The major conformational differences are localized, leading to one molecule being extended compared to the other. The collected crystal was twinned (twin ratio is 0.939:0.061), and the azide group is positionally disordered over two positions in one molecule [occupancy ratio 0.511 (18):0.489 (18)].

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Section: Related Literaturementioning

confidence: 99%

“…1). This structure is epimeric to the dimeric pentafluorophenyl ester with stereochemistry (3R,4R,5R) (Punzo et al, 2006) which was synthesized using D-ribose as starting material.…”

Section: S1 Commentmentioning

confidence: 99%

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

et al. 2010

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C-3 branched δ-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers

et al. 2011

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This article describes the efficient synthesis of the first generation of branched sugar amino acid (SAA) oligomers in solution phase via two main routes: by the use of a standard coupling reagent and via the use of active ester intermediates. Benzyl-protected dimeric carbopeptoid and methyl-protected dimeric and tetrameric, hexameric and octameric carbopeptoids were obtained from a branched δ-3,5-trans-tetrahydrofuran (THF) SAA and methyl-protected dimeric and tetrameric carbopeptoids were synthesised from a branched δ-3,5-cis-THF SAA. These systems are of interest because of their potential to display foldameric properties reminiscent of those observed in α-peptides and proteins. Amongst their many uses, foldamers provide simpler models in the study of the factors which induce the folding and unfolding of proteins and, ultimately, potential insights into their functioning.

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A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

et al. 2013

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This compendium focuses on functionalised sugar amino acids (SAAs) and their 3- to 6-membered nitrogen heterocyclic and carbocyclic analogues. The main benefit of using SAAs and their related nitrogen and carbon congeners in the production of peptidomimetics and glycomimetics is that their properties can be readily altered via modification of their ring size, chemical manipulation of their numerous functional groups and fine-tuning of the stereochemical arrangement of their ring substituents. These building blocks provide access to hydrophilic and hydrophobic peptide isosteres whose physical properties allow entry to a region of chemotherapeutic space which is still under-explored by medicinal chemists. These building blocks are also important in providing amino acids whose inherent conformational bias leads to predisposition to secondary structure upon oligomerisation in relatively short sequences. These foldamers, particularly those containing ω-amino acids, provide an additional opportunity to expand access to the control of structures by artificial peptides. The synthesis and biological evaluation of these building blocks in glycomimetics and peptidomimetics systems keep expanding the reach of the glycosciences to the medical sciences, provide a greater outlook onto the wide range of cellular functions of saccharides and their derivatives involved and greater insight into the nature of oligosaccharide and protein folding.

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Pentafluorophenyl (3R,4R,5R)-5-{[(3R,4R,5R)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carbonylamino]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

Cited by 3 publications

References 16 publications

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

Pentafluorophenyl (3R,4R,5S)-5-{[(3R,4R,5S)-5-azidomethyl-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxamido]methyl}-3,4-dimethoxy-2,3,4,5-tetrahydrofuran-3-carboxylate

C-3 branched δ-3,5-cis- and trans-THF sugar amino acids: synthesis of the first generation of branched homooligomers

A compendium of cyclic sugar amino acids and their carbocyclic and heterocyclic nitrogen analogues

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