108741-12-4

Upstream product

• 64-17-5 ethanol 
• 5695-95-4 (R)-2,3-Dihydroxy-3-phenyl-propionic acid 
• 18632-39-8 ethyl 2-hydroxy-3-phenyl-3-oxopropanoate 
• 103-36-6 ethyl 3-phenyl-2-propenoate 
• 2272-55-1 ethyl trans-3-phenyl-1-oxirane-2-carboxylate 
• 4192-77-2 ethyl cinnamate 
• 100-52-7 benzaldehyde 
• 4610-69-9 (Z)-ethyl cinnamate 
• 108739-49-7 (3S,5R,6S,9R)-3-((R)-Hydroxy-phenyl-methyl)-9-methyl-6-(1-methyl-1-phenyl-ethyl)-1,4-dioxa-spiro[4.5]decan-2-one 
• 133421-01-9 3-(Dimethylthexylsiloxy)-3-phenyl-2-(trimethylsiloxy)propannitril 
• 100-42-5 styrene 
• 140-88-5 ethyl acrylate 

Downstream Products

• 133521-66-1 (4S,5R)-Ethyl 2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carboxylate 
• 133421-02-0 erythro-2,2-Dimethyl-5-phenyl-1,3-dioxolan-4-carbonsaeure-ethylester 
• 16354-93-1 (1R,2R)-1-phenylpropane-1,2,3-triol 
• 130796-32-6 (4S,5R)-trans-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde 
• 130718-77-3 (4R,5R)-cis-2,2-dimethyl-5-phenyl-1,3-dioxolan-4-carbaldehyde 
• 133520-57-7 (4S,5R)-4-(hydroxymethyl)-2,2-dimethyl-5-phenyl-1,3-dioxolane 
• 133421-03-1 [1-((4R,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 133520-58-8 [1-((4S,5R)-2,2-Dimethyl-5-phenyl-[1,3]dioxolan-4-yl)-meth-(Z)-ylidene]-((R)-2-methoxymethyl-pyrrolidin-1-yl)-amine 
• 163893-32-1 (4S,5R)-2-Oxo-5-phenyl-2λ⁴-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester 
• 215544-03-9 (4R,5S)-ethyl 2,2-dimethyl-5-phenyl-1,3-dioxolane-4-carboxylate 
• 104713-12-4 (R)-1-phenylprop-2-en-1-ol 
• 153609-00-8 (4S,5S)-2,2-dimethyl-4-(hydroxymethyl)-5-phenyl-1,3-dioxolane 
• 185121-91-9 (4R,5S)-4-Iodomethyl-2,2-dimethyl-5-phenyl-[1,3]dioxolane 
• 1294479-60-9 ethyl (2S,3R)-3-hydroxy-2-(((4-nitrophenyl)sulfonyl)oxy)-3-phenylpropanoate 

Relevant academic research and scientific papers

Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles

A series of unprecedented binaphthyl–osmium nanoparticles (OsNPs) with chiral modifiers were applied in the heterogeneous asymmetric dihydroxylation of alkenes. A remarkable size effect of the OsNPs, depending on the density of the covalent organic shells, on the reactivity and enantioselectivity of the dihydroxylation reaction was revealed. Successful recycling of the OsNPs was also demonstrated and high reaction efficiency and enantioselectivity were maintained.

A soluble block copolymer-supported bis-cinchona alkaloid ligand for the asymmetric dihydroxylation of olefins

A soluble block copolymer-supported ligand was prepared via polycondensation of a bis-cinchona alkaloid derivative, polyethylene glycol, and terephthaloyl chloride. Its application in the asymmetric dihydroxylation of olefins delivered very good enantioselectivity.

A simple and effective soluble polymer-bound ligand for the asymmetric dihydroxylation of olefins: DHQD-PHAL-OPEG-OMe

The synthesis of a novel soluble polymer-bound ligand DHQD-PHAL-OPEG-OMe and its application in the catalytic asymmetric dihydroxylation (AD) reaction are described. 1,4-Dichlorophthalazine was used as the coupling reagent to connect dihydroquinidine and polyethylene glycol monomethyl ether (MW = 5000, Fluka) while providing an aromatic group at the 9-O-position of dihydroquinidine. Enantiomeric excesses for trans-disubstituted olefins in the AD reaction, with K3Fe(CN)6 as secondary oxidant, are up to 98%.

Catalytic asymmetric dihydroxylation of olefins using polysulfone-based novel microencapsulated osmium tetroxide

A polysulfone based novel polymer-supported osmium catalyst has been developed. The catalyst was prepared from commercially available polysulfone, based on a microencapsulation technique and was employed in the asymmetric dihydroxylation of various olefins using (DHQD)2PHAL as the chiral ligand and NMO as the co-oxidant in H2O-acetone-CH3CN (1:1:1). The catalyst was recovered by simple filtration and was reused to obtain excellent yields with good enantioselectivity up to five times.

Multipolymer-supported substrate and ligand approach to the sharpless asymmetric dihydroxylation

The correct combination of soluble and insoluble polymers allows a multipolymer reaction in which the substrate trans-cinnamate and the chiral ligand are bound to different polymer supports. The reactions (shown schematically on the right) proceed with 98

Total Synthesis of Aetheramide A

The first total synthesis of the highly potent anti-HIV natural product aetheramide A was accomplished in 18 steps from four equally complex building blocks. The synthesis established the unknown configuration at C26 and used a configurationally labile β-ketoester moiety for the self-adjustment of the configuration at a methyl branch. The pivotal macrolactamization was achieved by trapping a thermally generated acylketene which was derived from its corresponding dioxinone.

COVALENT RAS INHIBITORS AND USES THEREOF

The disclosure features compounds, or pharmaceutically acceptable salts thereof, alone and in combination with other therapeutic agents, pharmaceutical compositions, and protein conjugates thereof, capable of modulating biological processes including Ras, and their uses in the treatment of cancers.

RAS INHIBITORS

The disclosure features macrocyclic compounds, and pharmaceutical compositions and protein complexes thereof, capable of inhibiting Ras proteins, and their uses in the treatment of cancers.

Asymmetric Total Syntheses of Aetheramides and Their Stereoisomers: Stereochemical Assignment of Aetheramides

The concise total syntheses of the potent HIV inhibitors aetheramides A and B (IC50 values of 15 and 18 nM), as well as three pairs of their stereoisomers, were achieved, which allowed the complete stereochemical assignment of aetheramides for the first time. With a longest linear sequence of 15 steps, the convergent, fully stereocontrolled route provided aetheramides A and B in 5.3% and 3.6% yields, respectively. The synthetic strategy features efficient Stille coupling for macrocyclization, asymmetric aldol reactions to establish the ambiguous stereochemistries at C-17 and C-26, and implementation of mild conditions to avoid the epimerization of the sensitive polyketide moiety and the migration of the labile lactone.

Highly Enantioselective Iron-Catalyzed cis-Dihydroxylation of Alkenes with Hydrogen Peroxide Oxidant via an FeIII-OOH Reactive Intermediate

The development of environmentally benign catalysts for highly enantioselective asymmetric cis-dihydroxylation (AD) of alkenes with broad substrate scope remains a challenge. By employing [FeII(L)(OTf)2] (L=N,N′-dimethyl-N,N′-bis(2-methyl-8-quinolyl)-cyclohexane-1,2-diamine) as a catalyst, cis-diols in up to 99.8 % ee with 85 % isolated yield have been achieved in AD of alkenes with H2O2as an oxidant and alkenes in a limiting amount. This “[FeII(L)(OTf)2]+H2O2” method is applicable to both (E)-alkenes and terminal alkenes (24 examples >80 % ee, up to 1 g scale). Mechanistic studies, including18O-labeling, UV/Vis, EPR, ESI-MS analyses, and DFT calculations lend evidence for the involvement of chiral FeIII-OOH active species in enantioselective formation of the two C?O bonds.