- Bifunctional acyclic nucleoside phosphonates: synthesis of chiral 9-{3-hydroxy[1,4-bis(phosphonomethoxy)]butan-2-yl} derivatives of purines
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We report herein a general method for the synthesis of new types of chiral acyclic nucleoside four-carbon bisphosphonates. The alkylation of 2-amino-6-chloropurine and adenine was performed with (2S,3S)- or (2R,3R)-1,4-[bis(diisopropoxyphosphoryl)methoxy]]-3-[(methylsulfonyl)oxy]butan-2-yl benzoate. Alkylations provided (2R,3R) or (2S,3S) N9-substituted nucleobases, which were further converted to other derivatives. These conversions included either a modification of the nucleobase or transformation of the bisphosphonate chain. Subsequent deprotection of the diisopropyl esters with bromotrimethylsilane provided the resulting (2R,3R)- or (2S,3S)-bisphosphonic acids.
- Vrbkova, Silvie,Dracinsky, Martin,Holy, Antonin
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p. 2233 - 2247
(2008/02/11)
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- Polyhydroxylated azepanes as new motifs for DNA minor groove binding agents
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The synthesis of 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-phenoxy] and 1,3-bis-[3,4,5,6-tetrahydroxyazepane-N-p-benzyloxy] propanes is reported. These compounds have been prepared to investigate the potential of incorporating iminosugars as useful recognition elements in DNA minor groove binding agents. The compounds were shown to have very moderate binding affinities for DNA in thermal denaturation and ethidium bromide displacement assays when compared with propamidine. They were also found to possess some in vitro anticancer activity that did not correlate with their DNA binding affinity.
- Johnson, Heather A.,Thomas, Neil R.
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p. 237 - 241
(2007/10/03)
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- Highly Flexible Synthetic Routes to Functionalized Phospholanes from Carbohydrates
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Highly functionalized phospholanes 15, 17, and 26 and the corresponding diastereomers in which the configurations of the phospholane carbon-2 and carbon-5 are inverted can be readily prepared from D-mannitol by displacement of the appropriate dimesylate or cyclic sulfate with dilithium-phosphide reagents. The diols from which these ligands are prepared can also be converted into diarylphosphinite ligands. A route to related monophosphines bearing hemilabile tert-butylthio groups is also described. Complexes of these ligands and of related deprotected derivatives are potentially useful for enantioselective catalysis in organic and aqueous media.
- Yan, Yuan-Yong,RajanBabu
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p. 900 - 906
(2007/10/03)
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- SYNTHESIS AND CONFORMATIONS OF 2,3:4,5- AND 2,4:3,5-DI-O-ISOPROPYLIDENE-D-MANNITOL
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The 2,3:4,5- (8) and 2,4:3,5-di-O-isopropylidene (10) derivatives of D-mannitol have been prepared from 1,6-di-O-benzoyl-D-mannitol and their structures established by (13)C-n.m.r. spectroscopy.The 1,3-dioxane rings in 10 adopt a skew conformation and the sugar carbon chain in 8 is bent around the C-3-C-4 bond, as found by i.r. data and molecular mechanics calculations.Oxidation of 8 with pyridinium dichromate gave 2,3:4,5-di-O-isopropylidene-D-mannono-1,6-lactone (12).
- Gawronska, Krystyna
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- SYNTHESIS OF DIEPOXIDES AND DIAZIRIDINES, PRECURSORS OF ENANTIOMERICALLY PURE α-HYDROXY AND α-AMINO ALDEHYDES OR ACIDS, FROM D-MANNITOL
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Specific activations or protections of the hydroxyl groups of 3-4-O-isopropylidene-D-mannitol 2 followed by intramolecular SN2 reactions, lead to the chiral diepoxides 4 and 7 and to the chiral diaziridines 9 and 13 precursors of enantiomerically pure α-hydroxy and α-amino aldehydes or acids.
- Merrer, Yves Le,Dureault, Annie,Greck, Christine,Micas-Languin, Dominique,Gravier, Christine,Depezay, Jean-Claude
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p. 541 - 548
(2007/10/02)
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