摘要 |
PURPOSE: Optically active 2,6-disubstituted tetrahydropyran derivatives and a preparation method thereof are provided, which derivatives have various bio-stimulating activities such as antimicrobial, anticancer and antifungal activities. CONSTITUTION: The optically active 2,6-disubstituted tetrahydropyran derivatives of formula (I) are provided, wherein R1 is alkyl, aryl or aralkyl. The optically active 2,6-disubstituted tetrahydropyran derivatives of formula (II) are provided, wherein R1 is alkyl, aryl or aralkyl; and R2 is alkyl, aryl or aralkyl. The method for preparing asymmetric alcohol compound of formula (III) comprises reacting aldehyde of formula (V) with organic silicon tin compound of formula (IV) in the presence of (R)- or (S)-BINOL-Ti(OCH(CF3)2)2 complex as chiral Lewis acid catalyst at -80 to 0 deg. C. The method for preparing the optically active 2,6-disubstituted tetrahydropyran derivatives of formula (I) comprises circulation reaction of hydroxybromide compound of formula (III-a) in the presence of Ni(CO)2(PPh3)2 transition metal and triethylamine in fluoromethylbenzene. The method for preparing the optically active 2,6-disubstituted tetrahydropyran derivatives of formula (II) comprises reacting hydroxybromide compound of formula (III-a) in CH2Cl2 in the presence of n-methylmorpholine and propionic acid ester to prepare a compound of formula (III-b); and circulation reaction of the compound of formula (III-b) in radical reagent of AIBN/Bu3SnH and benzene.
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