22347-71-3Relevant academic research and scientific papers
Enantiopure purpurosamine C type glycosyl donors an improved access from rac-Acrolein dimer - Biocatalytic resolution
Erbeck, Silke,Prinzbach, Horst
, p. 2653 - 2656 (1997)
An improved synthetic access to a suitably 'protected' purpurosamine C type glycosyl donor (11, analogously ent-11) starting from racemic 3,4-dihydro-2H-pyran-2-carbaldehyde (rac-1, acrolein dimer) implies an 'indirect aziridination protocol' and a biocatalytic resolution step (acetate hydrolysis, ee > 98). The latter's stereochemical course is confirmed by a highly α-selective glycosylation with an acceptor of known absolute configuration.
Synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde: application to the synthesis of potent adenosine A2A and A3 receptor agonist
Jagtap, Prakash G.,Chen, Zhiyu,Koppetsch, Karsten,Piro, Elizabeth,Fronce, Paula,Southan, Garry J.,Klotz, Karl-Norbert
, p. 2693 - 2696 (2009)
Synthesis of potent adenosine A2A and A3 receptor agonist from the modification of adenosine-5′-N-ethylcarboxamide (NECA) has been reported. Diastereoisomer possessing an (R)-3,4-dihydro-2H-pyranyl (DHP) moiety exhibited the highest affinity at the A2A and A3 receptors. The key steps involve the synthesis of (R)-3,4-dihydro-2H-pyran-2-carboxaldehyde (7), which was obtained through the enzyme-catalyzed kinetic resolution of (±)-2-acetoxymethyl-3,4-dihydro-2H-pyran (5).
Photoinduced Fragmentation Borylation of Cyclic Alcohols and Hemiacetals
Aggarwal, Varinder K.,Madhavachary, Rudrakshula,Noble, Adam,Shu, Chao
supporting information, p. 7213 - 7218 (2020/10/12)
A visible-light photoinduced fragmentation borylation of O-phthalimido cycloalkanols with bis(catecholato)diboron is described. Structurally diverse keto and formyloxy alkyl boronic esters are shown to be conveniently prepared by radical-mediated ring opening of cyclic alcohols and hemiacetals, respectively. The reactions proceed under mild conditions in the absence of additives or photocatalysts, display excellent functional group tolerance, and are shown to allow cleavage of 4-, 5-, 6-, and 7-membered ring substrates. The mechanism proceeds via sequential homolytic N-O and C-C bond cleavages, the latter of which involves β-scission of an alkoxy radical, generating a carbonyl and an alkyl radical that is trapped by the diboron reagent. Spectroscopic studies suggest direct photoexcitation of either the phthalimide or diboron substrates with blue light can initiate a radical chain mechanism.
Antibody drug conjugate, intermediate, preparation method, pharmaceutical composition and uses thereof
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Page/Page column 183; 185, (2019/11/11)
Disclosed are an antibody drug conjugate IB, which uses ether linkages for connection, and improves the water solubility, stability and cytotoxicity in vivo and in intro, and an intermediate, a pharmaceutical composition, and uses of the antibody drug conjugate. The antibody drug conjugate has simple synthetic steps and a high yield.
AMINOGLYCOSIDES AND USES THEREOF
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Paragraph 00972, (2019/03/17)
Provided herein are aminoglycoside compounds, such as compounds of formula (I), (II), (III), (IV), (IVa), (V), (VI), (VIIa), or (VIIb) or pharmaceutically acceptable salts, solvates, stereoisomers, or tautomers of any of the foregoing, useful as therapeutic or prophylactic agents. Also provided herein are methods for their preparation. The compounds may be useful in treating a bacterial infection in a subject, for example a Gram-negative bacterial infection.
MODULAR SYNTHESIS OF AMINOGLYCOSIDES
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Paragraph 0640, (2019/10/29)
The present disclosure relates to novel methods for preparing antibacterial aminoglycoside compounds and the compounds used in such preparations.
SUBSTITUTED CYCLIC ETHER POLYMERS, AND CONJUGATES AND USES THEREOF
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Paragraph 0098, (2016/09/22)
Disclosed herein are substituted cyclic ether monomers, polymers, and drug conjugates thereof, which are useful for the treatment of diseases and conditions of the oral cavity. In particular, disclosed herein are monomers of Formula (I), polymers of Formu
Activity-Directed Synthesis with Intermolecular Reactions: Development of a Fragment into a Range of Androgen Receptor Agonists
Karageorgis, George,Dow, Mark,Aimon, Anthony,Warriner, Stuart,Nelson, Adam
supporting information, p. 13538 - 13544 (2015/11/11)
Activity-directed synthesis (ADS), a novel discovery approach in which bioactive molecules emerge in parallel with associated syntheses, was exploited to develop a weakly binding fragment into novel androgen receptor agonists. Harnessing promiscuous intermolecular reactions of carbenoid compounds enabled highly efficient exploration of chemical space. Four substrates were prepared, yet exploited in 326 reactions to explore diverse chemical space; guided by bioactivity alone, the products of just nine of the reactions were purified to reveal diverse novel agonists with up to 125-fold improved activity. Remarkably, one agonist stemmed from a novel enantioselective transformation; this is the first time that an asymmetric reaction has been discovered solely on the basis of the biological activity of the product. It was shown that ADS is a significant addition to the lead generation toolkit, enabling the efficient and rapid discovery of novel, yet synthetically accessible, bioactive chemotypes.
Direct C-H Trifluoromethylation of Glycals by Photoredox Catalysis
Wang, Bang,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 5698 - 5701 (2015/12/01)
A mild, efficient, and practical transformation for the direct C-H trifluoromethylation of glycals under visible light has been reported for the first time. This reaction employed fac-Ir3+(ppy)3 as the photocatalyst, Umemoto's reagent as the CF3 source, and a household blue LED or sunlight as the light source. Glycals bearing both electron-withdrawing and -donating protective groups performed this reaction smoothly. This visible light-mediated trifluoromethylation reaction was highlighted by the trifluoromethylation of the biologically important Neu2en moiety.
Steering reaction pathways: From benzyl Claisen rearrangements to powerful ionic shifts
Valerio, Viviana,Madelaine, Claire,Maulide, Nuno
supporting information; experimental part, p. 4742 - 4745 (2011/05/19)
Take a walk on the wild side: A novel benzyl Claisen cascade rearrangement of keteniminium salts is described. The reaction leads to α-arylated lactones under metal-free conditions (top scheme; Tf=trifluoromethanesulfonyl). It is further demonstrated that the cationic intermediates involved can be steered away from pericyclic reaction manifolds into powerful ionic shifts through reaction design (bottom scheme). Copyright
