10303-88-5Relevant academic research and scientific papers
AMINO-ACIDS AS CHIRAL SYNTHONS : SYNTHESIS OF ENANTIOMERICALLY PURE α-HYDROXY ESTERS.
Larcheveque, Marc,Petit, Yves
, p. 3705 - 3706 (1984)
Reaction of lithium homocuprates with α-hydroxy β-bromo ester derivated from aspartic acid affords α-hydroxy esters of high enantiomerical purity.
The synthesis of L-gulose and L-xylose from D-gluconolactone
Yang, Wen-Bin,Patil, Sachindra S,Tsai, Cheng-Hsin,Lin, Chun-Hung,Fang, Jim-Min
, p. 253 - 259 (2002)
L-Gulose, an essential component for the antibiotic and antitumor activities of bleomycin A2, was synthesized in 47% yield from D-glucono-1,5-lactone. The effective cleavage of acetonides by SnCl2 in the presence of tert-butyldimethylsilyl ethers was of importance in the course of synthesis. Elaboration of D-glucono-1,5-lactone that includes a step of oxidative degradation by Dess-Martin periodinane also afforded a respectable yield of L-xylose.
Determination of the absolute configuration of the glycerol component in poly(glycosylglycerolphosphates) by GLC-MS
Beynon,Richards
, p. 263 - 268 (1994)
Assignment of the stereochemistry of the glycerol residue in poly(glycosyl-glycerol phosphates) may be achieved by release of the chiral glycerol component, followed by its conversion to an appropriate derivative, and assignment of absolute stereochemistry by comparison with standards of known chirality.
Hydrolytic kinetic resolution of epoxides catalyzed by chromium(III)-endo, endo-2,5-diaminonorbornane-salen [Cr(III)-DIANANE-salen] complexes. Improved activity, low catalyst loading
Berkessel, Albrecht,Ertuerk, Erkan
, p. 2619 - 2625 (2006)
The hydrolytic kinetic resolution (HKR) of terminal epoxides, using chiral chromium(III)-salen catalysts based on DIANANE (endo,endo-2,5-diaminonorbornane) , was studied. A broad substrate scope was found for the chromium(III)-DIANANE catalysts, and very low loadings (down to 0.05 mol%) were needed to achieve high enantiomeric purities of both the remaining epoxides and the product diols (up to >99% ee). Besides monosubstituted epoxides, 2-methyl-2-n-pentyloxirane, which is an example for 2,2-disubstituted epoxides, could be ring-opened in an asymmetric fashion with water in the presence of an electronically tuned chromium-(III)-DIANANE complex.
d- and l-Serine, useful synthons for the synthesis of 24-hydroxyvitamin D3 metabolites. A formal synthesis of 1α,24R,25-(OH)3-D3, 24R,25-(OH)2-D3 and 24S,25-(OH)2-D3
Fernandez, Carlos,Gándara, Zoila,Gómez, Generosa,Covelo, Berta,Fall, Yagamare
, p. 2939 - 2942 (2007)
d- and l-Serine have been used for the enantioselective synthesis of tosylates 7a and 7b, useful building blocks for the synthesis of triols 5a and 5b which have already been obtained via a diastereoselective synthesis and used for the synthesis of 2a, 2b and 2c. We have thus performed a formal synthesis of 24S,25-(OH)2-D3, 24R,25-(OH)2-D3 and 1α,24R,25-(OH)3-D3.
Mechanistic Investigation Leads to a Synthetic Improvement in the Hydrolytic Kinetic Resolution of Terminal Epoxides
Nielsen, Lars P. C.,Stevenson, Christian P.,Blackmond, Donna G.,Jacobsen, Eric N.
, p. 1360 - 1362 (2004)
The mechanism of the hydrolytic kinetic resolution (HKR) of terminal epoxides was investigated by kinetic analysis using reaction calorimetry. The chiral (salen)Co-X complex (X = OAc, OTs, Cl) undergoes irreversible conversion to (salen)Co-OH during the course of the HKR and thus serves as both precatalyst and cocatalyst in a cooperative bimetallic catalytic mechanism. This insight led to the identification of more active catalysts for the HKR of synthetically useful terminal epoxides. Copyright
3-(Alkylthio)-1,2-bis(siloxy)-3-butenes as efficient chirality transferred building blocks
Masuya, Keiichi,Tanino, Keiji,Kuwajima, Isao
, p. 7965 - 7968 (1994)
In the presence of Me2AlCl, reactions of the title compounds with a variety of aldehydes proceeded with high efficacy of chirality transfer to give the corresponding optically pure ene adducts, which could be converted to the γ-lactones, e.g.,
A NEW APPROACH TO THE SYNTHESIS OF ETHER PHOSPHOLIPIDS. PREPARATION OF 1,2-DIALKYLGLYCEROPHOSPHORYLCHOLINES FROM L-GLYCERIC ACID
Bhatia, Suresh K.,Hajdu, Joseph
, p. 271 - 274 (1987)
A novel stereospecific synthesis of antitumor active ether phospholipids is reported.
Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation
Mallik, Suman,Prasad, Ramesh,Bhattacharya, Anindita,Sen, Prosenjit
supporting information, p. 434 - 439 (2018/05/23)
Natural phosphatidylserine (PS), which contains two chiral centers, enhances blood coagulation. However, the process by which PS enhanced blood coagulation is not completely understood. An efficient and flexible synthetic route has been developed to synthesize all of the possible stereoisomers of PS. In this study, we examined the role of PS chiral centers in modulating the activity of the tissue factor (TF)-factor VIIa coagulation initiation complex. Full length TF was relipidated with phosphatidylcholine, and the synthesized PS isomers were individually used to estimate the procoagulant activity of the TF-FVIIa complex via a FXa generation assay. The results revealed that the initiation complex activity was stereoselective and had increased sensitivity to the configuration of the PS glycerol backbone due to optimal protein-lipid interactions.
Synthesis and biological evaluation of enantiomerically pure glyceric acid derivatives as LpxC inhibitors
Tangherlini, Giovanni,Torregrossa, Tullio,Agoglitta, Oriana,K?hler, Jens,Melesina, Jelena,Sippl, Wolfgang,Holl, Ralph
, p. 1032 - 1044 (2016/02/19)
Inhibitors of the UDP-3-O-[(R)-3-hydroxymyristoyl]-N-acetylglucosamine deacetylase (LpxC) represent a promising class of novel antibiotics, selectively combating Gram-negative bacteria. In order to elucidate the impact of the hydroxymethyl groups of diol (S,S)-4 on the inhibitory activity against LpxC, glyceric acid ethers (R)-7a, (S)-7a, (R)-7b, and (S)-7b, lacking the hydroxymethyl group in benzylic position, were synthesized. The compounds were obtained in enantiomerically pure form by a chiral pool synthesis and a lipase-catalyzed enantioselective desymmetrization, respectively. The enantiomeric hydroxamic acids (R)-7b (Ki = 230 nM) and (S)-7b (Ki = 390 nM) show promising enzyme inhibition. However, their inhibitory activities do not substantially differ from each other leading to a low eudismic ratio. Generally, the synthesized glyceric acid derivatives 7 show antibacterial activities against two Escherichia coli strains exceeding the ones of their respective regioisomes 6.
