129574-09-0Relevant academic research and scientific papers
A deprotection procedure using SO3H silica gel to remove non-silyl protecting groups
Karaki, Fumika,Kuwada, Miki,Tajiri, Saki,Kanda, Misaki,Yanai, Mari,Kamimura, Mitsuhiro,Itoh, Kennosuke,Fujii, Hideaki
supporting information, p. 212 - 220 (2019/05/06)
Protecting groups are indispensable in organic synthesis and there is a great need for a variety of deprotection methods. Here, we investigated the scope of the application of a deprotection procedure using SO3H silica gel, which we have previously reported as a desilylation procedure. Under these conditions, -OMOM, -OSEM, -OTHP, and -OAc groups and dimethyl acetal were cleaved. Pivaloyloxy, benzyloxy and methoxy carbonyl groups remained intact and selective deprotection of TBS groups in the presence of other protecting groups was accomplished. We succeeded in cleaving an acetyl group on a secondary alcohol in a highly polar nortropine derivative. Our findings here provide another deprotection option and would be helpful in the synthesis of multifunctional compounds.
Suzuki-Miyaura cross-coupling of potassium alkoxyethyltrifluoroborates: Access to aryl/heteroarylethyloxy motifs
Fleury-Bregeot, Nicolas,Presset, Marc,Beaumard, Floriane,Colombel, Virginie,Oehlrich, Daniel,Rombouts, Frederik,Molander, Gary A.
, p. 10399 - 10408 (2013/01/15)
The introduction of an alkoxyethyl moiety onto aromatic substructures has remained a long-standing challenge for synthetic organic chemists. The main reasons are the inherent instability of alkoxyethylmetallic species and the lack of general procedures to access them. A new method utilizing a cross-coupling strategy based on the exceptional properties of organotrifluoroborates has been developed, and the method allows an easy and efficient installation of this unit on a broad range of aryl and heteroaryl bromides.
A fast and practical approach to tetrahydropyranylation and depyranylation of alcohols using indium triflate
Mineno, Tomoko
, p. 7975 - 7978 (2007/10/03)
Indium triflate-mediated tetrahydropyranylation of alcohols in dichloromethane and depyranylation of these products in aqueous methanol utilizing the same reagent but different molar ratio is described. In addition, indium triflate-promoted conversion of tetrahydropyran ethers to their corresponding acetates has also been described.
