Compositions and methods for cyclofructans as separation agents

摘要

The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.

主权项

1. A chiral stationary phase comprising:
a solid support; and a derivatized cyclofructan residue of formula I: wherein:n is 1-3;each L is, independently,
O—C(═O), orO—C(═O)—NR2,each R is, independently,H,(C1-C20)alkyl optionally substituted with 1-3 R1,(C3-C20)cycloalkyl optionally substituted with 1-3 R1,(C5-C50)aryl optionally substituted with 1-3 R1,heteroaryl optionally substituted with 1-3 R1,(C1-C20)alkoxy(C 1 -C20)alkyl,H2C═CH— (when L is O—C(═0)),H2C═C(CH3)— (when L is O—C(═0)),alkylenyl-N═C═O;arylenyl-N═C═O;(C5-C50)aryl(C1-C20)alkyl optionally substituted with 1-3 R1, orsaccharide residue lacking a hydroxyl group (when L is O), orcomprises a covalent bond to said solid support; R1 is, independently, (C1-C10)alkyl optionally substituted with 1-3 R6, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3; R2 is, independently, H or (C1-C10)alkyl; R3 is, independently, H or (C1-C10)alkyl; R4 is, independently, H or (C1-C10)alkyl; R5 is, independently, (C1-C20)alkyl optionally substituted with 1-3 R1, (C5-C50)aryl optionally substituted with 1-3 R1, or heteroaryl optionally substituted with 1-3R1; R6 is, independently, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3; wherein one to five R groups comprise covalent bonds to the solid support; and wherein the average degree of derivatization ranges from about 2 to about 7.