The stereoselective syntheses of 2,3-dideoxy-4-oxo-5a-carba-alpha- d-rhamnopyanose 1-phosphate, 2,3-dideoxy-5a-carba-alpha- d-rhamnopyranose 1-phosphate, 5a-carba-alpha- d-rhamnopyranose 1-phosphate, 5a-carba-beta- d-digitoxopyranose 1-phosphate, and 5a-carba-alpha- l-rhamnopyranose 1-phosphate have been achieved from d-quinic acid. The routes rely upon a Simmons-Smith cyclopropanation and diastereospecific ring opening of cyclopropanol under Pd/C hydrogenation condition to set up the alpha-methyl ketone. A sequence of diastereoselective reduction, dihydroxylation, and/or Myers' reductive 1,3-rearrangement were used to install the desired stereochemistry.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1021/ol801106r | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Polyproline-Polyornithine Diblock Copolymers with Inherent Mitochondria Tropism.
Adv Mater
January 2025
Príncipe Felipe Research Center, Polymer Therapeutics Lab., Valencia, 46012, Spain.
Mitochondria play critical roles in regulating cell fate, with dysfunction correlating with the development of multiple diseases, emphasizing the need for engineered nanomedicines that cross biological barriers. Said nanomedicines often target fluctuating mitochondrial properties and/or present inefficient/insufficient cytosolic delivery (resulting in poor overall activity), while many require complex synthetic procedures involving targeting residues (hindering clinical translation). The synthesis/characterization of polypeptide-based cell penetrating diblock copolymers of poly-L-ornithine (PLO) and polyproline (PLP) (PLO-PLP, n:m ratio 1:3) are described as mitochondria-targeting nanocarriers.
View Article and Find Full Text PDFA Wenzel Interfaces Design for Homogeneous Solute Distribution Obtains Efficient and Stable Perovskite Solar Cells.
Adv Mater
January 2025
College of Chemistry and Chemical Engineering/Film Energy Chemistry for Jiangxi Provincial Key Laboratory (FEC), Nanchang University, 999 Xuefu Avenue, Nanchang, 330031, China.
The coffee-ring effect, caused by uneven deposition of colloidal particles in perovskite precursor solutions, leads to poor uniformity in perovskite films prepared through large-area printing. In this work, the surface of SnO is roughened to construct a Wenzel model, successfully achieving a super-hydrophilic interface. This modification significantly accelerates the spreading of the perovskite precursor solution, reducing the response delay time of perovskite colloidal particles during the printing process.
View Article and Find Full Text PDFFine-Tuning the Physicochemical Properties of Poly(lactic Acid) Nanoparticles for the Controlled Release of the BET Inhibitor JQ1: Influence of PVA Concentration.
Polymers (Basel)
January 2025
Facultad de Farmacia-Centro de Innovación en Química Avanzada (ORFEO-CINQA), Unidad nanoDrug, Departamento de Química Inorgánica, Orgánica y Bioquímica, Universidad de Castilla-La Mancha, 02071 Albacete, Albacete, Spain.
The compounds targeting the bromo and extra terminal domain proteins (BET), such as the JQ1, present potent anti-cancer activity in preclinical models, however, the application of JQ1 at the clinical level is limited by its short half-life, rapid clearance, and non-selective inhibition of BET family proteins, leading to off-target effects and resistance. To address these challenges, the optimization of JQ1 delivery has been accomplished through polylactide (PLA) nanoparticles. PLA derivatives with varying molecular weights were synthesized via ring-opening polymerization using a zinc-based initiator and characterized using thermogravimetric analysis, differential scanning calorimetry, and infrared spectroscopy.
View Article and Find Full Text PDFPreparation, Optical, and Heat Resistance Properties of Phenyl-Modified Silicone Gel.
Polymers (Basel)
December 2024
Key Laboratory of Organosilicon Chemistry and Material Technology, College of Material, Chemistry and Chemical Engineering, Ministry of Education, Hangzhou Normal University, Hangzhou 311121, China.
A series of Si-H- or Si-Vi-terminated, branched and linear oligomers containing MeSiO segments were prepared by equilibrium polymerization or non-equilibrium polymerization initiated by living anions, respectively. These oligomers were used to improve the defects of concentrated crosslinking points and the high hardness of crosslinked products when using phenyltris(dimethylsiloxy)silane or 1,1,5,5-tetramethyl-3,3-diphenyl trisiloxane as crosslinking agents in the preparation of silicone gel. NMR, FT-IR, and GPC characterized the structure and molecular weight information of the prepared oligomers.
View Article and Find Full Text PDFThe Effect of Alkyl Substituents on the Formation and Structure of Homochiral (*,*)-[RGa(-OCH(Me)COR')] Species-Towards the Factors Controlling the Stereoselectivity of Dialkylgallium Alkoxides in the Ring-Opening Polymerization of -Lactide.
Molecules
January 2025
Faculty of Chemistry, Warsaw University of Technology, Noakowskiego 3, 00-664 Warsaw, Poland.
Building on our previous studies, which have demonstrated that homochiral propagating species-(*,*)-[MeGa(-OCH(Me)COR)]-were crucial for the heteroselectivity of [MeGa(-OCH(Me)COMe)] in the ring-opening polymerization (ROP) of racemic lactide (-LA), we have investigated the effect of alkyl groups on the structure and catalytic properties of dialkylgallium alkoxides in the ROP of -LA. Therefore, we have isolated and characterized the -[RGa(-OCH(Me)COMe] (R = Et (), Pr () and -[RGa(-OCH(Me)CHN] (R = Et (), Pr ()) complexes, to demonstrate the effect of alkyl groups on the chiral recognition induced the formation of the respective homochiaral species-(*,*)-[RGa(-OCH(Me)COMe)] and (*,*)-[RGa(-OCH(Me)CHN]. Moreover, we have investigated the structure of (,)-[RGa(-OCH(Me)COMe] (R = Et ((,)-, R = Pr ((,)-,) and their catalytic activity in the ROP of -LA.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!