101268-52-4Relevant articles and documents
Diastereoselective synthesis of (1,3-Dioxan-4-yl)pyrimidine and purin nucleoside analogues
Battisti, Umberto M.,Sorbi, Claudia,Quotadamo, Antonio,Franchini, Silvia,Tait, Annalisa,Schols, Dominique,Jeong, Lak Shin,Lee, Sang Kook,Song, Jayoung,Brasili, Livio
, p. 1235 - 1245 (2015)
(1,3-Dioxan-4-yl)-substituted nucleoside analogues, higher homologues of antiviral and anticancer 1,3-dioxolanes, were prepared from the key intermediate (4-acetoxy-1,3-dioxan- 2-yl)methyl benzoate and silylated bases. Glycosylation, carried out under Vorbrüggen conditions in the presence of trimethylsilyl trifluoromethanesulfonate (TMSOTf) as a catalyst, afforded the desired compounds with high stereoselecti- vity and regioselectivity, with only the desired β-anomeric N- 1 pyrimidine and N-9 purin nucleosides being obtained. 1H NMR experiments established that the β-anomers were diequatorial, and this assignment was confirmed by singlecrystal X-ray diffraction. Despite their structural similarities with natural nucleosides, none of the synthesized nucleosides showed antiviral activity.
A New and Versatile Synthesis of 1,3-Dioxan-5-yl-pyrimidine and Purine Nucleoside Analogues
Sorbi, Claudia,Prandi, Adolfo,Battisti, Umberto M.,Franchini, Silvia,Cornia, Andrea,Balzarini, Jan,Jeong, Lak Shin,Lee, Sang Kook,Song, Jayoung,Brasili, Livio
, p. 625 - 630 (2015)
1,3-Dioxan-5-yl pyrimidine and purine nucleoside analogues were prepared following a new and versatile synthetic strategy. These analogues were synthesized via nucleophilic addition of the selected nucleobase to a 1,3-dioxane scaffold that presents an appropriate leaving group in position 5. In particular cis and trans isomers of purine/pyrimidine nucleosides and their halogenated homologues were obtained. NMR experiments, carried out on the cis isomers, led to assignment of an equatorial orientation to the 2-hydroxymethyl group and axial orientation to the nucleobase in position 5 of the 1,3-dioxane. The trans isomers showed a diequatorial orientation of these groups. These assignments were confirmed by X-ray crystallographic studies.
Preparation of renieramycin left-half model compounds
Nakai, Keiyo,Kubo, Keiji,Yokoya, Masashi,Saito, Naoki
, p. 6529 - 6545 (2014)
Model compounds of the left-half of renieramycins, which are anticancer marine natural products having an α-aminonitrile functionality, were prepared from phenylalanine derivatives. The key step of the transformation is the stereospecific construction of 1,3-cis stereochemistry via an exomethylene intermediate. The stereoselective α-aminonitrile formation under kinetically controlled conditions is also discussed. The initial cytotoxicity profiles are presented.
Synthesis, structure, and conformational analysis of nucleoside analogues comprising six-membered 1,3-oxathiane sugar rings
Abou Assi, Hala,Martínez-Montero, Saúl,Dixit, Dilip M.,Chua, Zhijie,Bohle, D. Scott,Damha, Masad J.
, p. 1945 - 1953 (2015)
We report on the synthesis, characterization, and conformational analysis of 1,3-oxathiane nucleosides of both pyrimidine and purine nucleobases. The novel nucleoside analogues were prepared from readily available starting materials as α/β anomeric mixtur
IRAK DEGRADERS AND USES THEREOF
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Paragraph 00962; 003707-003709, (2020/06/19)
The present invention provides compounds, compositions thereof, and methods of using the same.
Aminoglycoside type derivative and preparing method and application thereof
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Paragraph 0069-0072, (2018/05/30)
The invention provides an aminoglycoside type derivative and a preparing method and application thereof. The aminoglycoside type derivative is a novel aminoglycoside type derivative. According to thederivative, the C2' amino position and the C6' amino pos
Diversity-oriented synthesis of cyclopropyl peptides from Ugi-derived dehydroalanines
Contreras-Cruz, David A.,Sánchez-Carmona, Miguel A.,Vengoechea-Gómez, Fabio A.,Pe?a-Ortíz, Daniel,Miranda, Luis D.
supporting information, p. 6146 - 6156 (2017/09/29)
A three-step synthesis of cyclopropyl peptides is reported. The protocol involves a consecutive Ugi-4CR/elimination reaction to prepare dehydroalanines followed by a Corey-Chaykovsky cyclopropanation reaction. Peptide-like molecules that resemble some pharmacologically active compounds with a variety of substituents in the cyclopropane ring were prepared. When (2-ethoxy-2-oxoethyl) dimethyl sulfonium ylide was used the reaction exclusively gives the cis-diastereoisomer cyclopropanes in good yields from readily prepared starting materials. A collection of 26 highly substituted cyclopropyl peptides were obtained.
Synthetic studies on saframycin anibiotics: an improved synthesis of tricyclic lactam intermediate and construction of the core ring system of saframycin A
Kimura, Shinya,Kawai, Shintaro,Azuma, Masayuki,Umehara, Yoshifumi,Koizumi, Yu-Ichi,Yokoya, Masashi,Saito, Naoki
, p. 327 - 343 (2015/03/04)
An improved synthesis of the tricyclic lactam intermediate of saframycin antibiotics and the construction of the core ring system having a cyano group at C-21 position were presented.1 The stereochemistry of several key intermediates was determined by X-r
Process for Manufacture of Optically Active 2-(Acyloxymethyl)-1,3-Oxathiolanes
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Page/Page column 9, (2012/06/30)
There is provided a process for manufacture of optically-active, 2-(acyloxymethyl)-1,3-oxathiolanes of Formula I comprising a preparation of a racemic compound and an enzyme-catalyzed kinetic resolution of the enantiomers. The invention may further provid
Process for Manufacture of Optically Active 2-(Acyloxymethyl)-1,3-Oxathiolanes
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, (2010/06/19)
There is provided a process for manufacture of optically-active, 2-(acyloxymethyl)-1,3-oxathiolanes of Formula I comprising a preparation of a racemic compound and an enzyme-catalyzed kinetic resolution of the enantiomers. The invention may further provide for the esterification and racemization of the by-product of the enzymatic reaction. In this manner, 2(R)-(benzoyloxymethyl)-1,3-oxathiolane is prepared as a useful intermediate for manufacture of the anti-HIV drug Apricitabine.
