Enantioselective Desymmetrization of FTY720

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 52–6...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 2014/10/01, Vol.62(10), pp.1041-1044
Hauptverfasser:	Hikawa, Hidemasa, Hamada, Maiko, Uchida, Yuka, Kikkawa, Shoko, Yokoyama, Yuusaku, Azumaya, Isao
Format:	Artikel
Sprache:	eng
Schlagworte:	Acylation asymmetric synthesis Benzoates - chemistry Catalysis Coordination Complexes - chemistry Copper - chemistry CuCl2 desymmetrization Fingolimod Hydrochloride FTY720 Oxazoles - chemistry Propylene Glycols - chemistry Solvents - chemistry Sphingosine - analogs & derivatives Sphingosine - chemistry Stereoisomerism tetraphenylbisoxazoline
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Beschreibung
Zusammenfassung:	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.
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.c14-00462