title: Enantioselective desymmetrization of FTY720.
abstract: A method for enantioselective desymmetrization of N-Ac and N-Boc-FTY720 by nonenzymatic asymmetric acylation was developed. Effective enantioselective monobenzoylation using benzoyl chloride in the presence of the tetraphenylbisoxazoline (L2)-CuCl2 complex gave the desired products 3a and 3b in 52-62% yield with 64% ee.
authors.affiliation: Faculty of Pharmaceutical Sciences, Toho University.
authors.forename: Hidemasa
authors.initials: H
authors.lastname: Hikawa
authors.forename: Maiko
authors.initials: M
authors.lastname: Hamada
authors.forename: Yuka
authors.initials: Y
authors.lastname: Uchida
authors.forename: Shoko
authors.initials: S
authors.lastname: Kikkawa
authors.forename: Yuusaku
authors.initials: Y
authors.lastname: Yokoyama
authors.forename: Isao
authors.initials: I
authors.lastname: Azumaya
mesh_terms: D000215:Acylation; D001565:Benzoates / Q000737:chemistry; D002384:Catalysis; D056831:Coordination Complexes / Q000737:chemistry; D003300:Copper / Q000737:chemistry; D000068876:Fingolimod Hydrochloride; D010080:Oxazoles / Q000737:chemistry; D011409:Propylene Glycols / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D001565:Benzoates; D056831:Coordination Complexes; D010080:Oxazoles; D011409:Propylene Glycols; D012997:Solvents; D003300:Copper; D000068876:Fingolimod Hydrochloride; D013110:Sphingosine; C029892:cupric chloride; C013409:benzoyl chloride