83458-87-1Relevant academic research and scientific papers
Preparation of optically active diol derivatives by the enzymatic hydrolysis of cyclic carbonates
Matsumoto, Kazutsugu,Fuwa, Seiji,Shimojo, Megumi,Kitajima, Hidehiko
, p. 2977 - 2987 (2007/10/03)
A simple enzymatic method for the preparation of optically active 1,2- and 1,3-diol derivatives is disclosed. In the screening of enzymes, racemic 4-[(2-benzyloxy)ethyl]-1,3-dioxolan-2-one (1a) was enantioselectively hydrolyzed by porcine pancreas lipase (PPL) to give optically active (R)-1a and (S)-4-(benzyloxy)butane-1,2-diol (2a). The addition of 10% i-PT2O to the reaction system dramatically improved the reactivity to afford optically pure (A)-1a in 31% yield. PPL also catalyzed the hydrolysis of several five-membered cyclic carbonates with high enatioselectivity. It is noteworthy that the increment of the carbon number of the substituents reflects the drastic increase in enantioselectivity. On the other hand, the hydrolyses of six- and seven-membered cyclic carbonates were also catalyzed by PPL. In particular, the reaction of a six-membered substrate enantioselectively proceeded. This reaction afforded optically active 1,3-diol derivatives which could not be directly prepared by hitherto known methods using hydrolytic enzymes.
Oligonucleotide analogs containing sulfur linkages
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, (2008/06/13)
Analogs of DNA containing sulfides, sulfoxides, and sulfones as linking groups between subunits capable of forming bonds with natural oligonucleotides are described. The analogs are lipophilic, stable to chemical degradation under a wide range of conditions and stable to enzymatic degradation in vivo.
REDUCTIVE RING OPENINGS OF ALLYL-ALCOHOL EPOXIDES
Finan, James M.,Kishi, Yoshito
, p. 2719 - 2722 (2007/10/02)
Red-Al reduction of allyl-alcohol epoxides was shown to yield 1,3-diols in high regioselectivity, while DIBAL reduction was shown to yield 1,2-diols.
REGIOSELECTIVE REDUCTIONS OF 2,3-EPOXY ALCOHOLS
Viti, Steven M.
, p. 4541 - 4544 (2007/10/02)
Regioselective reduction of 3-substituted-2,3-epoxy alcohols to 1,3-diols with sodium bis(2-methoxyethoxy)aluminum hydride (Red-al) is shown to be a general reaction for these substrates.
