Efficient mechanochemical synthesis of regioselective persubstituted cyclodextrins

• Laszlo Jicsinszky,
• Marina Caporaso,
• Katia Martina,
• Emanuela Calcio Gaudino and
• Giancarlo Cravotto

Beilstein J. Org. Chem. 2016, 12, 2364–2371, doi:10.3762/bjoc.12.230

• millimolar scale, they are easily scalable. Keywords: green chemistry; nucleophilic substitution; planetary ball mill; siRNA delivery intermediate; sugammadex; Introduction Cyclodextrins (CDs) are cyclic α(1→4)glucopyranosides and have been fully described in a number of publications [1][2][3]. They are

• -chloro-CDs [15] in solution. The solubility of per-6-halogeno-CDs is very limited in water and the majority of organic solvents, meaning that their preparation and purification is far from being environmentally friendly. Per-6-S-(3-mercapto)propionyl-γ-CD (Sugammadex, Bridion®) is not only the biggest

• higher amounts being employed, meaning it will likely soon become a generic molecule in most hospitals. The solventless preparation technique can provide clear advantages over classic methods since its use in humans requires very high purity. The standard preparation of Sugammadex uses a harsh base, such

Enabling technologies and green processes in cyclodextrin chemistry

• Giancarlo Cravotto,
• Marina Caporaso,
• Laszlo Jicsinszky and
• Katia Martina

Beilstein J. Org. Chem. 2016, 12, 278–294, doi:10.3762/bjoc.12.30

• preparation of CD thiols and thioethers is an emerging challenge because of the importance of intermediary azido derivatives [96] and favorable aggregation properties in nanomedicines and particularly the antidote Sugammadex [97]. The reaction between 6I-O-monotosyl-β-CD and various nucleophiles opens a new

Synthesis of uniform cyclodextrin thioethers to transport hydrophobic drugs

• Lisa F. Becker,
• Dennis H. Schwarz and
• Gerhard Wenz

Beilstein J. Org. Chem. 2014, 10, 2920–2927, doi:10.3762/bjoc.10.310

• compounds with very high binding potentials due to the higher hydrophobicity of sulfur compared to oxygen [21][22][23]. The octa-substituted carboxyethyl thioether of γ-CD is already in use under the name sugammadex (Bridion®) for the reversal of neuromuscular blockade, making use of its extremely high