111467-66-4Relevant articles and documents
Resolution of isopropylidene-glycerol benzoate by sequential enzymatic hydrolysis and preferential crystallization
Bianchi, Daniele,Bosetti, Aldo,Golini, Paolo,Cesti, Pietro,Pina, Carlo
, p. 817 - 819 (1997)
Both enantiomers of isopropylidene-glycerol are prepared from its benzoate ester with enantiomeric excess ≤95% by combined partially stereoselective lipase-catalyzed hydrolysis and preferential crystallization.
CYCLIC COMPOUND
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Paragraph 0335, (2018/04/13)
The present invention provides compounds having a Toll-like receptor 4 (TLR4) signaling inhibitory action useful as preventive and therapeutic drugs of autoimmune disease and/or inflammatory disease or diseases such as chemotherapy-induced peripheral neuropathy (CIPN), chemotherapy-induced neuropathic pain (CINP), liver injury, ischemia-reperfusion injury (IRI) and the like. The present invention relates to a compound represented by formula (I) and a salt thereof: (wherein, each symbol is explained in greater detail in the specification).
Fluoride-Catalyzed Esterification of Amides
Wu, Hongxiang,Guo, Weijie,Daniel, Stelck,Li, Yue,Liu, Chao,Zeng, Zhuo
supporting information, p. 3444 - 3447 (2018/02/21)
In recent years, it has been demonstrated that amide carbon–nitrogen bonds can be activated and selectively cleaved using transition metal catalysts. However, these methodologies have been restricted to specific amides; a one-to-one relationship exists between the catalytic system and the amides and also uses large amounts of transition-metal catalysts and ligands. Hence, we now report a general strategy for esterification of common amides using fluoride as a catalyst. This method shows high functional group tolerance, and notably it requires only a slight excess of the alcohol nucleophile, which is a rare case in transition-metal-free amide transformations. Moreover, this approach may provide a new understanding for further studies on esterification of amides and is expected to stimulate the development of alternative methods for direct functionalization of amides.
Asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5-carboxylic acid using a 1,2-addition of PhMgBr to an N-sulfinimine derived from (R)-glyceraldehyde acetonide and (S)-t-BSA
Babu, K. Chandra,Vysabhattar, Raman,Srinivas,Nigam, Satish,Madhusudhan,Mukkanti
experimental part, p. 2619 - 2624 (2011/01/05)
We report an asymmetric synthesis of (4S,5S)-2-oxo-4-phenyloxazolidine-5- carboxylic acid via stereoselective addition of phenylmagnesium bromide (PhMgBr) to an N-sulfinimine derived from (R)-glyceraldehyde acetonide. (S)- and (R)-Glyceraldehyde acetonides, important chiral synthons in synthetic organic chemistry, are prepared from the corresponding epichlorohydrin using an identical synthetic methodology.
Enhanced enantioselectivity of Bacillus coagulans in the hydrolysis of 1,2-O-isopropylidene glycerol esters by thermal knock-out of undesired enzymes
Romano, Diego,Falcioni, Francesco,Mora, Diego,Molinari, Francesco,Buthe, Andreas,Ansorge-Schumacher, Marion
, p. 841 - 845 (2007/10/03)
The enantioselective hydrolysis of different (RS)-1,2-O-isopropylidene glycerol esters has been achieved with whole cells of Bacillus coagulans NCIMB 9365 furnishing the (S)-alcohol as the major enantiomer. The reaction is catalysed by a thermostable cell-bound carboxylesterase and improvement of the enantioselectivity has been achieved by heat treatment of the whole cells, which causes the knock-outs a non-enantioselective competing enzyme. Thermally-treated cells hydrolysed (RS)-1,2-O-isopropylidene glycerol esters with high enantioselectivity, the highest enantiomeric ratio (80-100) being observed for the benzoate. The biocatalyst displayed good stability and could be re-used after filtration for 12 cycles before showing significant loss of activity; repeated biotransformation batches allowed the recovery of 9.55 g/L of enantiomerically pure (S)-isopropylideneglycerol benzoate starting from 24.0 g/L of the racemic mixture.
Organocatalytic kinetic resolution of racemic primary alcohols using a chiral 1,2-diamine derived from (S)-proline
Terakado, Dai,Koutaka, Hitomi,Oriyama, Takeshi
, p. 1157 - 1165 (2007/10/03)
A highly efficient and good enantioselective organocatalytic asymmetric acylation of racemic primary alcohols with acyl chlorides has been achieved catalyzed by a chiral 1,2-diamine derived from (S)-proline.
Stereoselective Syntheses of Both Enantiomers of Ketoconazole from (R)- and (S)-Epichlorohydrin
Camps, Pelayo,Farres, Xavier,Garcia, Luisa,Ginesta, Joan,Pascual, Jaume,et al.
, p. 1283 - 1294 (2007/10/03)
Stereoselective syntheses of both enantiomers of ketoconazole (1) from commercially available (R)- or (S)-epichlorohydrin has been developed.The key-step of syntheses involves the selective substitution of the methylene chlorine atom by benzoate on a mixture of (2S,4R)-14a and (2R,4R)-15a or of their enentiomers, followed by crystalization of the corresponding cis-benzoates, (2R,4R)-18 or (2S,4S)-18, from which (+)- or (-)-1 were obtained as described for (+/-)-1.The ee's of (+)- and (-)-ketocanazole were determined by HPLC on the CSP Chiracel OD-H.
Enatioselective Microbial Reduction of Monoesters of 1,3-Dihydroxypropanone: Synthesis of (S)- and (R)-1,2-O-Isopropylideneglycerol
Aragozzini, Fabrizio,Maconi, Elisabetta,Potenza, Donatella,Scolastico, Carlo
, p. 225 - 227 (2007/10/02)
The reduction of 3-benzoyloxy-1-hydroxypropanone with bakers' yeast proceeds enantioselectively to afford (S)-3-benzoyloxy-1,2-propanediol, which may be further converted into (S)-(benzoyloxymethyl)oxirane.The bioreduction with fermenting yeast of 1-acetoxy-3-benzyloxypropanones gives (R)-1-benzyloxy-3-acetoxy-2-propanol which can be used for the preparation of both (S)- and (R)-1,2-O-isopropylideneglycerol.
