A new and facile preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate
2007; Elsevier BV; Volume: 18; Issue: 20 Linguagem: Inglês
10.1016/j.tetasy.2007.09.026
ISSN1362-511X
AutoresFeng‐Lai Sun, Gang Xu, Jianping Wu, Lirong Yang,
Tópico(s)Enzyme Catalysis and Immobilization
ResumoA facile method for the preparation of tert-butyl (3R,5S)-6-hydroxy-3,5-O-isopropylidene-3,5-dihydroxyhexanoate is described by a chemoenzymatic approach. In this method, one hydroxyl stereocenter at C5 is obtained with a high ee value (up to 98.0%) via an enzymatic transesterification resolution of l-chloro-3-(4-methylbenzyloxy)-2-propanol. The other hydroxyl stereocenter at C3 was built with 98.0% de, by acid-hydrolysis of a 1,3-diol-acetonide syn/anti-10. It is noteworthy that the reduction of β-hydroxy ketone 8 with sodium borohydride can be carried out smoothly in aqueous isopropyl alcohol with a high diastereomeric ratio syn/anti (drs:a) of 4.0:1.
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