Synthesis of arabinose glycosyl sulfamides as potential inhibitors of mycobacterial cell wall biosynthesis

Synthesis and anti-mycobacterial activity of glycosyl sulfamides of arabinofuranose

“…The pyranose materials were found to predominate at equilibrium in aqueous solution. 12 Subsequent assays 13 of these materials against mycobacterial strains revealed only low to modest antibacterial activity; a result that was perhaps unsurprising given the existence of the materials in predominantly the pyranose, rather that the desired furanose form.…”

Direct Measurement of Rupture Force of Single Triazole Molecule by Atomic Force Microscope and Solid Phase Synthesis of Monodisperse Polyethylene Glycols

“…The synthetic route involving coupling 3.10 with 3.15 was used (Scheme 3.3). Relatively large amount of monomers 3.1, 27,28,[42][43]55 and 3.15 [50][51][52][53][54][55][56][57][58][59][60] was required for the synthesis and they were prepared using procedures similar to reported ones with slight but important modifications. Importantly, we did not purify any of the compounds with column chromatography, and impure monomers were used directly for the solid phase synthesis.…”

“…With this scale, theoretically 73 grams of 3.15 could be produced at the end of monomer synthesis. Although synthesis of the compound has been reported previously, [50][51][52][53][54][55][56][57][58][59][60] to minimize the formation of di-benzylated and depolymerized products [e.g. and cannot be easily seen but can be seen in ESI-MS ( Figure A.18).…”

“…13c, we coupled 3.10 with the monomer 3.15 to give 3.16 directly (Scheme 3.3) instead of using the route involving benzylation of 3.12. The required additional monomer 3.15 was prepared on small scale according to literature procedure [50][51][52][53][54][55][56][57][58][59][60]. Cleavage of 3.13c from 3.16 and tosylation of 3.13c to give 3.13e were achieved as described for 3.13b and 3.13d.…”

“…For the synthesis of BnO(PEG)4, in reported procedures, more equivalents NaH or other bases were generally used. Under those conditions, the yields of mono-benzylated product were usually around 70% or lower[50][51][52][53][54][55][56][57][58][59] although a few papers reported higher yields 60.…”