Influence of the N3‐Protection Group on N1‐ vs. O2‐Alkylation in the Mitsunobu Reaction

Ludek, Olaf R.; Meier, Chris

doi:10.1002/ejoc.200500801

Cited by 32 publications

(29 citation statements)

References 29 publications

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“…Therefore, the N3-position of thymine was protected with a benzoyl-(Bz-, 19) or a benzyloxymethyl- 20) as to avoid formation of the N3-regioisomer. 17 Despite using the conditions for the Mitsunobu reaction as recommended by Rejman and coworkers,16 no product was obtained. Further attempts to optimize the reaction conditions proved fruitless.…”

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confidence: 99%

Elaboration of a proprietary thymidylate kinase inhibitor motif towards anti-tuberculosis agents

Song

Risseeuw

Froeyen

et al. 2016

Bioorganic & Medicinal Chemistry

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International audienceWe report the design and synthesis of a series of non-nucleoside MtbTMPK inhibitors (1-14) based on the gram-positive bacterial TMPK inhibitor hit compound 1. A practical synthesis was developed to access these analogues. Several compounds show promising MtbTMPK inhibitory potency and allow the establishment of a structure-activity relationship, which is helpful for further optimization

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confidence: 99%

Elaboration of a proprietary thymidylate kinase inhibitor motif towards anti-tuberculosis agents

Song

Risseeuw

Froeyen

et al. 2016

Bioorganic & Medicinal Chemistry

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“…We prepared the N-deprotected building block in five steps and 26 % overall yield. The Mitsunobu reaction [23] of 14 -easily assembled through the reduction of a diprotected iminodiacetic acid -with the known N 3 -benzoylthymine [24] gave thyminated adduct 15. This we deprotected at the two nitrogen atoms in the presence of trifluoroacetic acid to yield α-amino ester 16.…”

Section: Computational Studiesmentioning

confidence: 99%

Design, Synthesis, and Hybridisation of Water‐Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine

Zarra¹,

Montesarchio²,

Coppola³

et al. 2009

Eur J Org Chem

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The preparation of a new class of backbone-modified PNA\ud mimetic incorporating thymine is described. Target dipeptoid\ud monomer 21 was synthesised from an N-[2-(thymin-1-yl)ethyl]\ud glycinate ester and a properly protected iminodiacetic\ud acid. The distinctive structural motif in the backbone is a\ud carboxy group, inserted to impart water solubility to the\ud oligomer. Two achiral oligopeptoid sequences (8-mer and 12-\ud mer), characterised by the shift of the amide carbonyl group\ud away from the nucleobase, were efficiently assembled according\ud to solid-phase synthesis protocols. Thermal denatur-ation studies showed that the two homopyrimidine oligopeptoids\ud do not effectively hybridise with complementary sequences\ud of DNA and RNA or fully synthetic (2,4-diamino)-\ud triazin-6-yl-tagged peptoid 22. A possible reason could reside\ud in the concurrent unfavourable influence of the anionic\ud N-(carboxymethyl) moieties and the flexible nucleobase/\ud backbone ethylene linker

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“…N3-Benzoylated thymine 3 26,27 was coupled to 4-iodobenzenboronic acid to afford the known N1-(4-iodophenyl)thymine derivative 4 28 and further converted to the corresponding boronic ester 5 28 using methodology developed by Gothelf and co-workers. 28,29 By using similar procedures, also the m-substituted isomers 6 and 7 were obtained in good yields.…”

Section: Synthesismentioning

confidence: 99%

Double-headed nucleotides introducing thymine nucleobases in the major groove of nucleic acid duplexes

et al. 2015

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Four different double-headed nucleosides each combining two thymine nucleobases with different linkers were synthesised. The 5-position of 2'-deoxyuridine was connected to the N1-position of a thymine through either m- or p-disubstituted phenyl or phenylacetylene linkers by the use of Suzuki or Sonogashira couplings. When introduced into oligonucleotides, the thermal stability of dsDNA and DNA : RNA duplexes were determined and structural information was obtained from CD- and fluorescence spectroscopy. Also the recognition of abasic sites was studied. In general, the more stable duplexes were obtained with m- rather than p-substitution and with phenylacetylene rather than phenyl linkers.

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Influence of the N3‐Protection Group on N1‐ vs. O²‐Alkylation in the Mitsunobu Reaction

Cited by 32 publications

References 29 publications

Elaboration of a proprietary thymidylate kinase inhibitor motif towards anti-tuberculosis agents

Elaboration of a proprietary thymidylate kinase inhibitor motif towards anti-tuberculosis agents

Design, Synthesis, and Hybridisation of Water‐Soluble, Peptoid Nucleic Acid Oligomers Tagged with Thymine

Double-headed nucleotides introducing thymine nucleobases in the major groove of nucleic acid duplexes

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