13504-85-3Relevant articles and documents
A recyclable and highly stereoselective multi-fluorous proline catalyst for asymmetric aldol reactions
Gotoh, Machiko,Ishihara, Kazuki,Ishihara, Kotaro,Kobayashi, Yuki,Matsugi, Masato,Obayashi, Riho,Shioiri, Takayuki,Watanabe, Yuki
, (2020)
A recyclable fluorous proline catalyst with high stereoselectivity that functions as a catalyst for asymmetric aldol reactions is described. Its high stereoselectivity and facile recovery are achieved by employing a multi-fluorous tag attachment strategy. Although a gradual decrease was observed with respect to the catalytic activity, the catalyst can be separated from the reaction mixture by adsorption onto FluoroFlash and can be reused in that form for a maximum of five times while maintaining a high stereoselectivity.2019 Elsevier Ltd. All rights reserved.
An improved synthesis of (lS,4S)-2-oxa-5-azabicyclo[2.2.1]heptane
Zhang, Dong-Feng,Li, Peng,Lin, Zi-Yun,Huang, Hai-Hong
, p. 479 - 481 (2014)
An improved and efficient method for synthesis of (lS,4S)-2-oxa-5- azabicyclo[2.2.1]heptane (1) from trans-4-hydroxy-l-proline was developed. Using benzyloxycarbonyl (Cbz) as protection group of amine, the reactions were in mild conditions, and the title compound 1 was accomplished in six steps in overall yield of 70%.
Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices
Horng, Jia-Cherng,Hsu, Kuang-Cheng,Li, Meng-Che,Lin, Chih-Wei,Lin, Tse-Hsueh,Liu, Ying-Jie,Wang, Sheng-Kai
, (2021/11/30)
The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.
Practical Gram-Scale Synthesis of Iboxamycin, a Potent Antibiotic Candidate
Mason, Jeremy D.,Myers, Andrew G.,Pote, Aditya R.,Terwilliger, Daniel W.
supporting information, p. 11019 - 11025 (2021/08/03)
A gram-scale synthesis of iboxamycin, an antibiotic candidate bearing a fused bicyclic amino acid residue, is presented. A pivotal transformation in the route involves an intramolecular hydrosilylation-oxidation sequence to set the ring-fusion stereocenters of the bicyclic scaffold. Other notable features of the synthesis include a high-yielding, highly diastereoselective alkylation of a pseudoephenamine amide, a convergent sp3-sp2 Negishi coupling, and a one-pot transacetalization-reduction reaction to form the target compound's oxepane ring. Implementation of this synthetic strategy has provided ample quantities of iboxamycin to allow for its in vivo profiling in murine models of infection.
