16361-14-1Relevant articles and documents
Synthesis of a protected derivative of (±)-1-(hydroxymethyl)conduritol C from 2-(hydroxymethyl)furan
Arjona, Odon,Iradier, Fatima,Manas, Rosario M.,Plumet, Joaquin
, p. 8335 - 8336 (1998)
A short and totally stereoselective synthesis of a protected derivative of (±)-1-(hydroxymethyl)conduritol C has been achieved. The key step was the cleavage of the oxygen bridge in a 7-oxanorbomenic sulfone using an acidic medium.
Transition-Metal-Free and Base-Promoted Carbon-Heteroatom Bond Formation via C-N Cleavage of Benzyl Ammonium Salts
Liu, Long,Tang, Yuanyuan,Wang, Kunyu,Huang, Tianzeng,Chen, Tieqiao
, p. 4159 - 4170 (2021/03/09)
A facile and general method for constructing carbon-heteroatom (C-P, C-O, C-S, and C-N) bonds via C-N cleavage of benzyl ammonium salts under transition-metal-free conditions was reported. The combination of t-BuOK and 18-crown-6 enabled a wide range of substituted benzyl ammonium salts to couple readily with different kinds of heteroatom nucleophiles, i.e. hydrogen phosphoryl compounds, alcohols, thiols, and amines. Good functional group tolerance was demonstrated. The scale-up reaction and one-pot synthesis were also successfully performed.
Open-Close Strategy toward the Organocatalytic Generation of 2-Deoxyribosyl Oxocarbenium Ions: Pyrrolidine-Salt-Catalyzed Synthesis of 2-Deoxyribofuranosides
Ghosh, Titli,Mukherji, Ananya,Kancharla, Pavan K.
, p. 7488 - 7498 (2019/11/29)
The reaction of secondary amine salts with 2-deoxy-ribofuranoses under forcible conditions leads to the putative furanosyl oxocarbenium ion that is trapped with various alcohols to provide 2-deoxy-ribofuranosides. The observed anomeric selectivities range from an equimolar mixture to complete α-selectivity in the case of bulky sugar acceptors. Owing to the mechanism and temperature of the transformation, the generated oxocarbenium ion shows little or no facial preference towards the nucleophilic attack of non-carbohydrate acceptors and leads to a mixture of anomers in the case of benzyl and acetyl protected donors. However, the conformationally less flexible tetraisopropylsilyl protected donor reacted with both sugar and non-sugar acceptors in a stereoselective fashion. Besides, the glycosylation with 2-cyanoethanol gave the product with unexpected beta-selectivity presumably due to nitrile effect. The operationally simple organocatalytic protocol provides easy access to otherwise difficult 2-deoxy-ribofuranosides/disaccharides.
JAK2 JH2 Fluorescence Polarization Assay and Crystal Structures for Complexes with Three Small Molecules
Newton, Ana S.,Deiana, Luca,Puleo, David E.,Cisneros, José A.,Cutrona, Kara J.,Schlessinger, Joseph,Jorgensen, William L.
supporting information, p. 614 - 617 (2017/06/13)
A competitive fluorescence polarization (FP) assay is reported for determining binding affinities of probe molecules with the pseudokinase JAK2 JH2 allosteric site. The syntheses of the fluorescent 5 and 6 used in the assay are reported as well as Kd results for 10 compounds, including JNJ7706621, NVP-BSK805, and filgotinib (GLPG0634). X-ray crystal structures of JAK2 JH2 in complex with NVP-BSK805, filgotinib, and diaminopyrimidine 8 elucidate the binding poses.
