In 2019,Angewandte Chemie, International Edition included an article by Aota, Yusuke; Kano, Taichi; Maruoka, Keiji. Reference of 1,4,7,10,13-Pentaoxacyclopentadecane. The article was titled 《Asymmetric Synthesis of Chiral Sulfoximines through the S-Alkylation of Sulfinamides》. The information in the text is summarized as follows:
Innovation in drug discovery critically depends on the development of new bioisosteric groups. Chiral sulfoximines, which contain a tetrasubstituted sulfur atom that bears one nitrogen, one oxygen, and two different carbon substituents, represent an emerging chiral bioisostere in medicinal chem. Chiral sulfoximines are conventionally prepared by a stereospecific nitrene transfer reaction to chiral sulfoxides; however, the number of readily available chiral sulfoxides remains limited. Herein, we report the asym. synthesis of a class of hitherto difficult-to-access chiral sulfoximines with two structurally similar alkyl chains. Our synthetic approach is based on the sulfur-selective alkylation of easily accessible chiral sulfinamides with com. available reagents under simple and safe conditions. This stereospecific S-alkylation offers a general and scalable approach to the asym. synthesis of chiral sulfoximines, which represent important substructures in bioactive mols. The experimental part of the paper was very detailed, including the reaction process of 1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5Reference of 1,4,7,10,13-Pentaoxacyclopentadecane)
1,4,7,10,13-Pentaoxacyclopentadecane(cas: 33100-27-5) is a member of crown ether Ligands. Crown-ethers are macrocyclic polyethers capable of forming host-guest complexes, especially with inorganic and organic cations. Crown-ethers can incorporate protonated primary amine compounds by formation of ion-dipole bonds with the oxygen atoms of the chiral selector. Crown-ethers have been widely used for the separation of several pharmaceuticals both in aqueous and non-aqueous media. Reference of 1,4,7,10,13-Pentaoxacyclopentadecane
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem