133095-74-6Relevant academic research and scientific papers
Synthesis of enantiomerically pure 3-butene-1,2-diol derivatives via a Sharpless asymmetric epoxidation route
Neagu,Hase
, p. 1629 - 1630 (1993)
A short enantiospecific synthesis of the butenediol monotosylates (1,2), the epoxybutanediol monotosylates (3,4) and the epoxybutenes (5,6) is described.
Enzyme-mediated enantioselective hydrolysis of 1,2-diol monotosylate derivatives bearing an unsaturated substituent
Matsumoto,Oohana,Hashimoto,Usuda,Shimoda,Ohshima,Suzuki,Togawa
, p. 3981 - 3988 (2018/06/15)
We have succeeded in the easy preparation of optically active 1,2-diol monotosylates bearing an unsaturated substituent via enzymatic hydrolysis. Lipase PS quickly catalyzes the hydrolyses of 2-acetoxybut-3-enyl tosylate, which has a double bond, and 2-acetoxybut-3-ynyl tosylate, which has a triple bond, with excellent enantioselectivity to afford the corresponding optically active compounds. The reaction is also applicable to acetates with a longer chain, which has a double bond at the terminus. To demonstrate the applicability of this method, enantiomerically pure (R)-massoialactone, a natural coconut flavor, has been synthesized from racemic 2-acetoxypent-4-enyl tosylate in several steps. Furthermore, the enzyme can recognize the stereochemistry of olefins, and the (Z)-alkenyl structure is more suitable for the enantioselective hydrolysis than the (E)-isomer.
Synthesis of the C1-C15 fragment of elaiolide
Jhillu Singh, Yadav,Rao Yarrapothu, Gangadhara,Vemula, Rajender
, p. 55 - 58 (2013/03/29)
The synthesis of the C1-C15 fragment of elaiolide was achieved by successfully utilizing the desymmetrization strategy, zirconium catalyzed C-C bond formation and double stereodifferentiating aldol reactions. The Royal Society of Chemistry.
Stereoselective preparation of a key intermediate toward the synthesis of nelfinavir
Raghavan, Sadagopan,Kumar, Ch. Naveen
experimental part, p. 821 - 828 (2011/08/09)
A stereoselective synthesis of an intermediate that can be elaborated into the potent HTV-protease inhibitor, nelfinavir, is described. The key step of the reaction sequence is the stereoselective preparation of a bromosulfonamide from an olefin using the
Three step synthesis of single diastereoisomers of the vicinal trifluoro motif
Brunet, Vincent A.,Slawin, Alexandra M. Z.,O'Hagan, David
supporting information; experimental part, (2010/04/22)
A three step route to single diastereoisomers of the vicinal trifluoromethyl motif is described. The route starts from either syn- or anti-α,β-epoxy alcohols and takes a direct approach in that each of the three steps introduces a fluorine atom in a regio- and stereospecific manner. Starting from either the syn- or the anti-α,β-epoxy alcohol, stereospecific reactions generate two separate diastereoisomeric series of this motif. The route is a significant improvement on an earlier six step strategy.
New synthesis of sn-1,2- and sn-2,3-O-diacylglycerols application to the synthesis of enantiopure phosphonates analogous to triglycerides: A new class of inhibitors of lipases
Marguet, Frank,Cavalier, Jean-Francois,Verger, Robert,Buono, Gerard
, p. 1671 - 1678 (2007/10/03)
Phosphonate compounds mimic the first transition state occurring during enzymatic carboxyester hydrolysis of natural substrates by forming a covalent bond with the catalytic serine. However, until now the organophosphorus compounds used in the inhibition studies more or less resembled a natural triglyceride substrate. In order to elucidate the interfacial activation and the mechanism of action of lipases, specific inhibitors need to be prepared. To achieve this goal, enantiomerically pure sn-1,2- and sn-2,3O- didecanoylglycerol compounds were prepared - starting from a C-4 chiral synthon, 3-buten-1,2-diol - and treated with n-pentylphosphonic dichloride and p-nitrophenol to afford the corresponding diastereomeric phosphonates, which were acylglycerol analogs. Subsequent separation of each of the phosphonate diastereomers A/B or ent-A/ent-B, performed by HPLC, led to four enantiopure stereoisomers that will be investigated as inhibitors of Human Pancreatic Lipase (HPL) and Human Gastric Lipase (HGL) using the monomolecular film technique.
Amine assisted enzymatic esterification of 1,2-diol monotosylates
Boaz,Zimmerman
, p. 153 - 156 (2007/10/02)
The enzymatic esterification of 1,2-diol monotosylates in organic solvent under standard conditions often fails to achieve the desired 50% conversion due to enzyme inactivation by acidic contaminants. The inclusion of an amine affords rapid conversion to
Alcohol-ester sparation by reaction with acetate
-
, (2008/06/13)
A process is disclosed for the isolation of an enantiomerically enriched alcohol from a first mixture of an enantiomerically enriched 1-arylsulfonate-2 -hydroxy-3-butene and an enantiomerically enriched 1 -arylsulfonate- 2-acyloxy-3-butene. The process includes the steps of: (a) contacting the mixture with a reagent capable of reacting with said 1-arylsulfonate-2-hydroxy-3-butene to remove the arylsulfonate group and produce a mixture of dihydroxybutene monoesters thereby forming a second mixture containing said dihydroxybutene monoesters and unreacted enantiomerically enriched 1-arylsulfonate-2-acyloxy-3-butene (b) contacting the second mixture with reagents capable of hydrolyzing all of the acyl groups in said mixture to hydroxy groups so as to produce a third mixture comprising 1,2-dihydroxy-3-butenes and enantiomerically enriched 1-arylsulfonate-2-hydroxy-3 -butene; (c) washing said third mixture with water so as to remove said 1,2-dihydroxy-3-butenes.
Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: Efficient chirality transfer
Oppolzer, Wolfgang,Birkinshaw, Timothy N.,Bernardinelli, Gerald
, p. 6995 - 6998 (2007/10/02)
S-4-Acetoxy-6-aza-2,8-nonadienes 9 and 11 were subjected to Pd(0)-catalyzed cyclizations. The S,E-acetate 9 gave exclusively S,E-pyrrolidine 12, whereas the antipodal product R,E-12 was formed from the S,Z-precursor 11 (Scheme 3). X-ray-diffraction analys
