71697-18-2Relevant academic research and scientific papers
Resolution of a racemic 1,2-diol using triphenylmethyl protection of the primary hydroxyl group and Mucor miehei lipase (Lipozyme) for the kinetic resolution
Petursson, Sigthor,Jonsdottir, Sigridur
, p. 1809 - 1812 (2011)
The triphenylmethyl group gives very simple access to the 1-protection of 1,2-diol as exemplified by racemic propane-1,2-diol. This group has, however, been shown to be incompatible with lipases commonly used for the resolution of alcohols. This turned out to be the case for Pseudomonas cepacia lipase, which we have used in our earlier work. Lipozyme, a Mucor miehei lipase, best known for 1,3-selectivity with glycerol is, however, shown to catalyze transacetylation onto the secondary hydroxyl group next to a triphenylmethoxy group. The transacetylation is completely enantioselective for the (R)-enantiomer giving a very simple method for the resolution of this type of 1,2-diol enantiomer.
Immobilized lipase screening towards continuous-flow kinetic resolution of (±)-1,2-propanediol
Aguillón, Anderson R.,Avelar, Marcelo N.,Gotardo, Larissa E.,de Souza, Stefania P.,Le?o, Raquel A.C.,Itabaiana, Ivaldo,Miranda, Leandro S.M.,de Souza, Rodrigo O.M.A.
, p. 128 - 134 (2019/02/12)
Here, we report a flow chemistry approach for kinetic resolution of (±)-1,2-propanediol protected by trityl group using the packed-bed reactor filled with different immobilized enzymes. It was investigated the performance of 16 immobilized lipases, includ
Continuous-Flow Synthesis of (R)-Propylene Carbonate: An Important Intermediate in the Synthesis of Tenofovir
Suveges, Nicolas S.,Rodriguez, Anderson A.,Diederichs, Carla C.,de Souza, Stefania P.,Le?o, Raquel A. C.,Miranda, Leandro S. M.,Horta, Bruno A. C.,Pedraza, Sérgio F.,de Carvalho, Otavio V.,Pais, Karla C.,Terra, José H. C.,de Souza, Rodrigo O. M. A.
supporting information, p. 2931 - 2938 (2018/06/27)
(R)-Propylene carbonate is an important intermediate in the synthesis of tenofovir pro-drugs such as tenofovir alafenamide fumarate (TAF) and tenofovir diisoproyl fumarate (TDF). Independent of the pro-drug type, tenofovir presents a chiral secondary hydroxy derivative, which can be obtained directly from (R)-propylene carbonate. Herein, we report our chemo-enzymatic continuous-flow strategy towards (R)-propylene carbonate starting from a very cheap and renewable raw material, glycerol. We were able to synthesize (R)-propylene carbonate in seven continuous-flow steps, starting from glycerol, in good-to-excellent yields (66–93 %) and excellent selectivity (E > 200).
N-Substituted Benzenepropanamide and Benzenepropenamide For Use in the Prevention or the Treatment of Affective Disorders
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Paragraph 0094, (2014/09/30)
Compounds for use in the treatment or prophylaxis of an affective disorder, which compound is represented by formula I in which the dotted line represents a single or a double bond; and R5 and R5′ are independently —H, —OH or —OR6, where R6 is a linear or branched C1-C4 alkyl; X is —CH2O—; Z is —CH2OH2O—, —CH(CH3)CH2O— or —CH2CH(CH3)O—; m is 1; and n is an integer of 1-5; or a pharmaceutically acceptable salt, prodrug, metabolite, or hydrate thereof.
N- SUBSTITUTED BENZENEPROPANAMIDE AND BENZENEPROPENAMIDE FOR USE IN THE PREVENTION OR THE TREATMENT OF AFFECTIVE DISORDERS
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Page/Page column 25; 26, (2013/04/10)
Compounds for use in the treatment or prophylaxis of an affective disorder, which compound is represented by formula I in which the dotted line represents a single or a double bond; and R5 and R5' are independently -H, -OH or -OR6, where R6 is a linear or branched C1-C4 alkyl; X is -CH2O-; Z is -CH2ΟΗ2O-,-CH(CH3)CH2O- or -CH2CH(CH3)O-; m is 1; and n is an integer of 1-5; or a pharmaceutically acceptable salt, prodrug, metabolite, or hydrate thereof.
Palladium-catalyzed asymmetric quaternary stereocenter formation
Gottumukkala, Aditya L.,Matcha, Kiran,Lutz, Martin,De Vries, Johannes G.,Minnaard, Adriaan J.
supporting information; experimental part, p. 6907 - 6914 (2012/07/01)
An efficient palladium catalyst is presented for the formation of benzylic quaternary stereocenters by conjugate addition of arylboronic acids to a variety of β,β-disubstituted carbocyclic, heterocyclic, and acyclic enones. The catalyst is readily prepared from PdCl2, PhBOX, and AgSbF 6, and provides products in up to 99 % enantiomeric excess, with good yields. Based on this strategy, (-)-α-cuparenone has been prepared in only two steps. Copyright
Large scale monotritylations of water soluble compounds containing multiple hydroxyl groups
Kaats-Richters,Zwikker,Keegstra,Jenneskens
, p. 2399 - 2409 (2007/10/02)
A procedure for the large scale monotritylation of watersoluble substrates containing multiple hydroxylgroups is reported; no elaborate purification procedures are required.
