- Compound a preparation (1R, 2S, 6S, 7S) - 4, 4 - dimethyl -9 - phenylmethyl - 3, 5, 8 - trioxa -9 - aza tricyclic[5.2.1.02.6][...] method
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The invention discloses a method for preparing a compound (1R,2S,6S,7S)-4,4-dimethyl-9-benzyl-3,5,8-trioxa-9-azatricyclo[5.2.1.0]decane. The method comprises steps: (1) mixing a compound with the chemical structure shown as a formula 1 and zinc in a protic solvent, so as to obtain a compound with the chemical structure shown as a formula 2; (2) mixing the compound with the chemical structure shown as the formula 2 and benzylhydroxylamine or a salt thereof in a protic solvent in the presence of an inorganic base, so as to obtain a compound with the chemical structure shown as a formula 3, wherein the inorganic base is selected from sodium carbonate, potassium carbonate or sodium bicarbonate; and (3) refluxing the compound with the chemical structure shown as the formula 3 in chlorobenzene in the presence of a base, so as to obtain a compound with the chemical structure shown as a formula 4, wherein the base is selected from potassium carbonate, sodium carbonate, sodium bicarbonate, pyridine and triethylamine.
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- Synthesis of Aminocyclopentanetriol Derivatives
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The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor. The present invention provides in particular a process for the preparation of a compound of formula V comprising: a) providing a compound of formula IV , and b) reducing the compound of formula IV with activated zinc in the presence of copper to give the compound of formula V.
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- SYNTHESIS OF TRIAZOLOPYRIMIDINE COMPOUNDS
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The present invention relates to the field of organic synthesis and describes the synthesis of specific intermediates suitable for the preparation of triazolopyrimidine compounds such as ticagrelor.
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- Synthesis and biological evaluation of ticagrelor derivatives as novel antiplatelet agents
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Ticagrelor (1) is the first reversible P2Y12 receptor antagonist blocking adenine diphosphate (ADP)-induced platelet aggregation with rapid onset and offset of effects. In this study, synthesis of ticagrelor and its derivatives has been accomplished in a convergent way. The compound design was based on modifications of ticagrelor and its major metabolite (33) in order to ameliorate their pharmacokinetic properties and dosing profile. The final compounds (1a-g, 35a-g) were evaluated for their inhibitory effect on ADP-induced platelet aggregation in rats. The assay results showed that some compounds (e.g., 1b, 1d, 33, 35b, 35f) exhibited comparable potency with that of ticagrelor.
- Zhang, Hao,Liu, Jun,Zhang, Luyong,Kong, Lingyi,Yao, Hequan,Sun, Hongbin
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p. 3598 - 3602
(2012/07/14)
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- An improved approach to chiral cyclopentenone building blocks. Total synthesis of pentenomycin I and neplanocin A
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An improved approach to enantiomerically pure hydroxylated cyclopentenones is reported here, which involves intramolecular nitrone cycloaddition of sugar-derived chiral pent-4-enals and hex-5-en-ones-2 followed by N-O bond cleavage, quaternization of the amine thus produced, and finally oxidative elimination of the amino group. Synthesis of pentenomycin I and neplanocin A is described following this methodology.
- Gallos, John K.,Stathakis, Christos I.,Kotoulas, Stefanos S.,Koumbis, Alexandros E.
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p. 6884 - 6890
(2007/10/03)
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- Expeditoious Synthesis of Aminocyclopentitols from D-Ribose via Intramolecular Nitrone Cycloaddition
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The synthesis of 4α-aminocyclopentane-1α,2β,3β-triol (a key-intermediate in the preparation of carbocyclic nucleosides) and its N-substituted derivatives, has been achieved by the intarmolecular nitrone cycloadditions of a γ-unsaturated aldehyde, easily accessible from D-ribose, followed by reductive N-O bond cleavage in the resulting bicyclic oxazanes.
- Gallos, John K.,Goga, Efthymia G.,Koumbis, Alexandros E.
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p. 613 - 614
(2007/10/02)
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