10.1021/jo00317a030
The study investigates the synthesis and properties of substituted 2,6-dioxabicyclo[3.1.1]heptanes, specifically focusing on the compounds 1,3-anhydro-2,4,6-tri-O-benzyl-β-D-mannopyranose and 1,3-anhydro-2,4,6-tri-O-(p-bromobenzyl)-β-D-mannopyranose. These compounds are synthesized through a series of reactions involving various reagents such as dibutyltin oxide, allyl bromide, benzyl chloride, and p-bromobenzyl bromide. The synthesis process includes steps like acetylation, benzylation, and ring closure using strong bases like sodium hydride (NaH) and potassium tert-butoxide (t-BuOK). The study aims to produce these anhydro sugars as precursors for the synthesis of 1,3-mannopyranans by ring-opening polymerizations, which are of interest for their potential applications in immunological and biochemical investigations. The compounds' structures are confirmed through mass spectrometry, 1H NMR, and 13C NMR spectroscopy, and their stability and purity are assessed through various analytical techniques.
10.1039/b003789n
The research focuses on synthesizing and analyzing the conformational behavior of an eight-membered lactam dipeptide. The purpose was to study self-recognition and dimerization in cis-disubstituted medium-ring lactam dipeptides as a part of designing β-turn mimetics. The synthesis involved 12 steps starting from L-serine-derived compounds, yielding the dipeptide with a semi-extended conformation capable of head-to-tail dimerization (Kdim ~ 100 dm3/mol in CDCl2CDCl2). Conformational analyses using NMR, IR, and vapour pressure osmometry revealed strong intermolecular interactions. Chemicals used included L-serine-derived oxazolidines, dibutyltin oxide, di-tert-butyl dicarbonate, and diphenylphosphoryl azide, among others.
10.1016/j.tetlet.2009.11.026
The study focuses on enhancing the efficiency of the selective monotosylation of 1,2-diols using dibutyl tin oxide (Bu2SnO) as a catalyst. The researchers discovered that the amount of Bu2SnO could be significantly reduced from 2 mol % to as low as 0.005 mol % while still achieving effective tosylation. They also found that the corresponding tin acetal 3b, derived from Bu2SnO and ethylene glycol, exhibited faster conversions and more reproducible reaction times compared to Bu2SnO alone. The study highlights the use of diisopropyl ethyl amine (iPr2NEt) as a base, which provided better purity of the product than triethylamine (Et3N). The research demonstrates that the tin acetal 3b can be used as a generic catalyst for selective diol tosylation, allowing further reduction in catalyst loading and achieving higher yields and better selectivities on various commercial diol substrates.