Optimized methods for preparation of 6^I-(ω-sulfanyl-alkylene-sulfanyl)-β-cyclodextrin derivatives

Abstract

SummaryA general high-yielding method for the preparation of monosubstituted β-cyclodextrin derivatives which have attached a thiol group in position 6 is described. The thiol group is attached through linkers of different lengths and repeating units (ethylene glycol or methylene). The target compounds were characterized by IR, MS and NMR spectra. A simple method for their complete conversion to the corresponding disulfides as well as a method for the reduction of the disulfides back to the thiols is presented. Both, thiols and disulfides are derivatives usable for well-defined covalent attachment of cyclodextrin to gold or polydopamine-coated solid surfaces.

Pentafluorobenzene end-group as a versatile handle for para fluoro “click” functionalization of polythiophenes

“…in K 2 CO 3 and THF for 12 h at 40 °C under argon, thus opening the door for reversible crosslinking and self-healing using disulfide bond formation. 91 We note that the PFB moiety was found to undergo three SNAr reactions when reacted with an excess of ODT in DMF for 2 hours at room temperature, as evidenced by MALDI-TOF and the two doublets at high chemical shifts in the 19 F NMR (see ESI † ). As a proof of concept, the ODT-functionalized P3EPT–PFB was oxidized to the disulfide using CuCl and triethylamine at 50 °C in chlorobenzene for 12 h. The GPC elugram of the oxidized polymer clearly demonstrates the doubling of molecular weight of a majority of polymer chains ( Fig.…”

Dual-channel recognition of Al3+ and Cu2+ ions using a chiral pyrene-based fluorescent sensor

“…Silica gel 60 N (spherical, neutral, 63–210 μm) was used for column chromatography. Diethylene glycol bis( p -toluenesulfonate), 49 (2-((3 R ,7a S )-2-phenylhexahydro-1 H -pyrrolo[1,2- c ]imidazol-3-yl)phenyl)bis(3-(trifluoromethyl)phenyl)methanol ( 4 ), 40 and 1,1′-bipyrene ( 6 ) 47 were synthesized according to the literature procedures. A hexane solution of diethylzinc (1.1 M, Kanto Chemical Co., Inc., Japan) was used for the enantioselective addition.…”

Monosubstituted Cyclodextrins as Precursors for Further Use

“…Although some authors do not purify the product, it is recommended the crude product be treated by chromatography [148,151,159] or recrystallised from water [149,152,153,157] or 50 % MeOH in H 2 O. [160,161] Subsequent substitution of the tosyl CD derivative with sodium azide is carried out in water [148][149][150]159] or DMF. [147,152,157] The final step, when the amine is formed, involves reduction with triphenylphosphine in the presence of aqueous ammonia [148,152,159] or water.…”