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• W2053046119 endingPage "1893" @default.
• W2053046119 startingPage "1882" @default.
• W2053046119 abstract "Enzymatic resolution of racemic 1,4,5,6-tetrachloro-2-(hydroxymethyl)-7,7-dimethoxybicyclo[2.2.1]hept-5-ene (rac-1) using various lipases in vinyl acetate as acetyl source was studied. The obtained enantiomerically enriched (+)-(1,4,5,6-tetrachloro-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-yl)methyl acetate ((+)-2; 94% ee), upon treatment with Na in liquid NH3, followed by Amberlyst-15 resin in acetone, provided (−)-5-(hydroxymethyl)bicyclo[2.2.1]hept-2-en-7-one ((−)-7), which is a valuable precursor for the synthesis of carbasugar derivatives. Subsequent Baeyer–Villiger oxidation afforded a nonseparable mixture of bicyclic lactones, which was subjected to LiAlH4 reduction and then acetylation. The resultant compounds (−)-11 and (+)-12 were submitted to a cis-hydroxylation reaction, followed by acetylation, to afford the novel carbasugar derivatives (1S,2R,3S,4S,5S)-4,5-bis(acetoxymethyl)cyclohexane-1,2,3-triyl triacetate ((−)-(13)) and (1R,3R,4R,6R)-4,6-bis(acetoxymethyl)cyclohexane-1,2,3-triyl triacetate ((−)-(14)), respectively, with pseudo-C2-symmetric configuration. The absolute configuration of enantiomerically enriched unreacted alcohol (−)-1 (68% ee) was determined by X-ray single-crystal analysis by anchoring optically pure (R)-1-phenylethanamine. Based on the configurational correlation between (−)-1 and (+)-2, the absolute configuration of (+)-2 was determined as (1R,2R,4S)." @default.
• W2053046119 created "2016-06-24" @default.
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• W2053046119 date "2010-10-01" @default.
• W2053046119 modified "2023-10-14" @default.
• W2053046119 title "Enzyme-Catalyzed Stereoselective Synthesis of Two Novel Carbasugar Derivatives" @default.
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• W2053046119 doi "https://doi.org/10.1002/hlca.201000213" @default.
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