109240-73-5Relevant academic research and scientific papers
Facile synthesis of C2-symmetric chiral crown ethers with two reactive hydroxymethyl groups
Nakatsuji, Yohji,Nakahara, Yoshio,Nagamiya, Katsumori,Itoh, Yuki,Uesugi, Kentaro,Ishida, Naohisa,Muraoka, Masahiro,Kida, Toshiyuki,Akashi, Mitsuru
, p. 2973 - 2978 (2007)
Two C2-symmetric chiral crown ethers, (2S,12S)-2,12- bis(hydroxymethyl)-2,12-dimethyl-18-crown-6 and (2R,9R)-2,9-bis(hydroxymethyl)- 2,9-dimethyl-18-crown-6 were synthesized from a chiral subunit, [(45)-2,2,4-trirnethyl-1,3-dioxolane-4-yl]methanol, at high enantiomeric purity over several steps. This synthetic method offers the potential to construct a variety of C2-symmetric chiral crown ethers using diverse combinations of building blocks. Georg Thieme Verlag Stuttgart.
Enantiocomplementary chemoenzymatic asymmetric synthesis of (R)- And (S)-chromanemethanol
Fuchs, Michael,Simeo, Yolanda,Ueberbacher, Barbara T.,Mautner, Barbara,Netscher, Thomas,Faber, Kurt
experimental part, p. 833 - 840 (2009/07/05)
A non-lipase-based, enantiocomplementary chemoenzymatic route towards enantiopure (R)- and (S)-chromane-methanol (12), which are the key building blocks for the synthesis of stereoisomerically pure α-tocopherols, has been achieved by the biocatalytic reso
Bacillus subtilis epoxide hydrolase-catalyzed preparation of enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether and its application to expeditious synthesis of (R)-bicalutamide
Fujino, Aya,Asano, Masayoshi,Yamaguchi, Hitomi,Shirasaka, Naoki,Sakoda, Akiko,Ikunaka, Masaya,Obata, Rika,Nishiyama, Shigeru,Sugai, Takeshi
, p. 979 - 983 (2008/02/04)
Expeditious synthesis of (R)-bicalutamide (1), a synthetic antiandrogen, from enantiopure 2-methylpropane-1,2,3-triol monobenzyl ether (4) was achieved. An engineered Bacillus subtilis epoxide hydrolase worked enantioselectively on the racemic epoxide (7) to provide the above starting material in highly enantiomerically enriched state.
Selectivity enhancement of enantio- and stereo-complementary epoxide hydrolases and chemo-enzymatic deracemization of (±)-2-methylglycidyl benzyl ether
Simeo, Yolanda,Faber, Kurt
, p. 402 - 409 (2007/10/03)
The kinetic resolution of (±)-2-methylglycidyl benzyl ether was achieved via enantioselective biohydrolysis using microbial and plant epoxide hydrolases. Depending on the type of enzyme, opposite enantiopreference and stereo-complementary mode of action (
5-Methyl-4H-1,3-dioxins, new chiral building blocks: Transformation into (R)- and (S)-4-hydroxymethyl-4-methyl-1,3-dioxolanes via oxidation and rearrangement and determination of the absolute configuration
Flock, Susanne,Frauenrath, Herbert,Wattenbach, Carsten
, p. 3394 - 3399 (2007/10/03)
5-Methyl-4H-1,3-dioxins obtained by asymmetric double-bond isomerization have been transformed into 4-hydroxymethyl-4-methyl-1,3-dioxolanes by m-chloroperbenzoic acid oxidation, ring contraction and reduction. The stereochemical course of this transformat
Chemo-enzymatic enantioconvergent synthesis of C4-building blocks containing a fully substituted chiral carbon center using bacterial epoxide hydrolases
Steinreiber,Hellstr?m,Mayer,Orru,Faber
, p. 111 - 113 (2007/10/03)
A highly efficient chemo-enzymatic asymmetric synthesis of chiral C4-building blocks containing a fully substituted carbon center is reported. The key transformation consists of a deracemization based on an enantioconvergent asymmetric hydrolys
Enantioselective hydrolysis of functionalized 2,2-disubstituted oxiranes with bacterial epoxide hydrolases
Steinreiber, Andreas,Osprian, Ingrid,Mayer, Sandra F.,Orru, Romano V. A.,Faber, Kurt
, p. 3703 - 3711 (2007/10/03)
The biohydrolysis of 2,2-disubstituted oxiranes bearing various oxygen functional groups was investigated using the epoxide hydrolase activity of 11 bacterial strains. The results show that the activity and the selectivity strongly depend on the substrate structure and the biocatalyst. Whereas substrates possessing free hydroxyl groups were not transformed, their analogs, protected as ethers, were well accepted. This allowed the convenient modulation of the enantioselectivity by proper choice of the ether group according to size and polarity. It was found that the distance of the ether-oxygen to the stereogenic quaternary carbon center of the oxirane ring had a profound influence on the enantioselectivity, and several oxiranes were resolved with good to excellent selectivities. The enantiomerically enriched epoxides and vicinal diols thus obtained contain a useful 'synthetic handle' in their side chain, which allows their use as building blocks in asymmetric synthesis.
ASYMMETRIC SYNTHESIS OF (R)-(+)- AND (S)-(-)-2,2,4-TRIMETHYL-4-(HYDROXYMETHYL)-1,3-DIOXOLANE OF HIGH ENANTIOMERIC PURITY
Tanner, David,Somfai, Peter
, p. 5985 - 5990 (2007/10/02)
The title compounds, 1 and 1', are readily available in four steps from 2-benzyloxymethyl-2-propen-1-ol, the key step being Sharpless asymmetric epoxidation to give the chiral epoxides 5 or 5'.The total chemical yield of 1 or 1' is 50percent, the final pr
