Category: 929-37-3

On September 17, 2001, Stavenger, Robert A.; Schreiber, Stuart L. published an article.SDS of cas: 929-37-3 The title of the article was Asymmetric catalysis in diversity-oriented organic synthesis: Enantioselective synthesis of 4320 encoded and spatially segregated dihydropyrancarboxamides. And the article contained the following:

Dihydropyrancarboxylates were prepared on solid-phase by stereoselective and enantioselective hetero Diels-Alder cycloaddition of β,γ-unsaturated-α-keto esters to resin-bound vinyl ethers in the presence of nonracemic copper bis(oxazoline) catalysts as intermediates in the preparation of an encoded combinatorial library of dihydropyrancarboxamides. Hydroxy-substituted vinyl ethers were prepared; the vinyl ethers were attached by treatment of silyl-substituted polystyrene resin macrobeads with triflic acid followed by addition of the hydroxy-substituted vinyl ethers to the resin-bound silyl triflate; the resin-bound vinyl ethers were treated with chloroarom. diazoketones in the presence of dirhodium tetraacetate to give tagged resin-bound vinyl ethers which could be later identified by LC-MS. Treatment of resin-bound vinyl ethers such as I with the heterodienes (E)-RCH:CHCOCO2CH2CH:CH2 (R = Me2CH, Ph, 2-fluorenyl, 4-MeO2CC6H4, 5-benzo-1,3-dioxolanyl, 3-thienyl, 3-benzofuranyl, 1-acetyl-3-indolyl, 4-oxo-3-benzopyranyl, 1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydropyrazolyl) in the presence of the bis(oxazoline) II (or its enantiomer) and copper (II) triflate followed by cleavage of the resin with HF•pyridine gives nonracemic dihydropyrancarboxylates such as III (or their enantiomers) in >5:1 diastereoselectivities and >30:1 enantioselectivities. The resin-bound dihydropyrancarboxylates could be tagged with a second chloroarom. diazoketone, deallylated with tetrakis(triphenylphosphine)palladium and thiosalicylic acid in THF, coupled with primary and secondary amines with the benzotriazolyloxyphosphonium salt PyBOP and diisopropylethylamine, and cleaved from the resin with HF•pyridine to give an encoded combinatorial library of natural product-like nonracemic dihydropyrancarboxamides (no data). E.g., treatment of the silyl-substituted polystyrene resin with triflic acid followed by the addition of sulfonamide-substituted vinyl ether I with lutidine gave a resin-bound vinyl ether; the vinyl ether resin was added to unsaturated ketoester (E)-Me2CHCH:CHCOCO2CH2CH:CH2 and mol. sieves under argon; addition of THF and a solution of II and copper triflate in THF and stirring gave a resin-bound nonracemic dihydropyrancarboxylate which was cleaved from the resin with HF•pyridine to give III in >95% purity and in >16:1 diastereo- and enantioselectivities. Cleavage of a subset of the dihydropyrancarboxamide-containing beads and anal. by LC-MS indicated that 104 of the 108 sample compounds were isolated in >75% purity. The use of asym. synthesis of natural product-like libraries on encoded beads allows for the use of stereochem. as a diversity element in the preparation of combinatorial libraries; the prepared libraries are produced in a form amenable to robot-controlled biol. testing. The experimental process involved the reaction of 2-(2-(Vinyloxy)ethoxy)ethanol(cas: 929-37-3).SDS of cas: 929-37-3

The Article related to dihydropyrancarboxylate stereoselective enantioselective preparation intermediate combinatorial library, dihydropyrancarboxamide stereoselective enantioselective preparation combinatorial library, copper bisoxazoline catalyst enantioselective cycloaddition unsaturated ketoester vinyl ether and other aspects.SDS of cas: 929-37-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

On November 4, 2016, Lansakara, Ashabha I.; Mariappan, S. V. Santhana; Pigge, F. Christopher published an article.Synthetic Route of 929-37-3 The title of the article was Alkylidene Dihydropyridines As Synthetic Intermediates: Model Studies toward the Synthesis of the Bis(piperidine) Alkaloid Xestoproxamine C. And the article contained the following:

Results of model studies demonstrating a stereoselective synthetic route to tricyclic analogs of the bis(piperidine) alkaloid xestoproxamine C are presented. Dearomatization of a tricyclic pyridine derivative to afford an alkylidene dihydropyridine (anhydrobase) intermediate followed by catalytic heterogeneous hydrogenation was used to install the correct relative stereochem. about the bis(piperidine) ring system. Other key features of these model studies include development of an efficient ring-closing metathesis procedure to prepare macrocyclic derivatives of 3,4-disubstituted pyridines, intramol. cyclizations of alkylidene dihydropyridines to establish pyridine-substituted pyrrolidines and piperidines, successful homologation of pyridine-4-carboxaldehydes using formaldehyde di-Me thioacetal monoxide (FAMSO), and application of B-alkyl Suzuki coupling to assemble substituted pyridines. The experimental process involved the reaction of 2-(2-(Vinyloxy)ethoxy)ethanol(cas: 929-37-3).Synthetic Route of 929-37-3

The Article related to xestoproxamine c analog stereoselective synthesis alkylidenedihydropyridine intermediate model study, dearomatization tricyclic pyridine derivative alkylidenedihydropyridine, stereoselective hydrogenation alkylidenedihydropyridine, ring closing macrocyclization xestoproxamine c analog synthesis and other aspects.Synthetic Route of 929-37-3

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

On January 31, 2000, Coalter, Joseph N. III; Bollinger, John C.; Huffman, John C.; Werner-Zwanziger, Ulrike; Caulton, Kenneth G.; Davidson, Ernest R.; Gerard, Helene; Clot, Eric; Eisenstein, Odile published an article.Safety of 2-(2-(Vinyloxy)ethoxy)ethanol The title of the article was Coordinated carbenes from electron-rich olefins on RuHCl(PPri3)2. And the article contained the following:

Dehydrohalogenation of RuH2Cl2L2 (L = PPri3) gives (RuHClL2)2, shown to be a halide-bridged dimer by x-ray crystallog.; the fluoride analog is also a dimer. (RuHClL2)2 reacts with N2, pyridine and C2H4 (L’) to give RuHClL’L2, but with vinyl ether and vinyl amides, H2C:CH(E) [E = OR, NRC(O)R’] such olefin binding is followed by isomerization to the heteroatom-substituted carbene complex L2HClRu:CMe(E). The reaction mechanism for such rearrangement was established by DFT (B3PW91) computations, for C2H4 as olefin (it is endothermic), and the structures of intermediates are calculated for H2C:C(H)(OCH3) and for cyclic and acyclic amide-substituted olefins. It is found, both exptl. and computationally, that the amide O is bonded to Ru, with a calculated bond energy of ∼9 kcal mol-1 for an acyclic model. Less electron-rich vinyl amides or amines form η2-olefin complexes, but do not isomerize to carbene complexes. Calculated ΔE values for selected competition reactions reveal that donation by both Ru and the heteroatom-substituted X are necessary to make the carbene complex L2HClRu:C(X)Me more stable than the olefin complex L2HClRu(η2-H2C:CHX). This originates in part from a diminished endothermicity of the olefin → carbene transformation when the sp2 C bears a π-donor substituent. The importance of a hydride on Ru in furnishing a mechanism for this isomerization is discussed. The compositional characteristics of Schrock and Fischer carbenes are detailed, it is suggested that reactivity will not be uniquely determined by these characteristics, and these new carbenes RuHCl[C(X)CH3]L2 are contrasted to Schrock and Fischer carbenes. The experimental process involved the reaction of 2-(2-(Vinyloxy)ethoxy)ethanol(cas: 929-37-3).Safety of 2-(2-(Vinyloxy)ethoxy)ethanol

The Article related to crystal structure ruthenium hydrido dinitrogen carbene complex, mol structure ruthenium hydrido dinitrogen carbene complex, electron rich olefin ruthenium coordinated regioselective rearrangement, vinyl amide ether ruthenium coordinated regioselective rearrangement, density functional ruthenium coordinated olefin regioselective rearrangement and other aspects.Safety of 2-(2-(Vinyloxy)ethoxy)ethanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem

On September 17, 2001, Blackwell, Helen E.; Perez, Lucy; Schreiber, Stuart L. published an article.Recommanded Product: 2-(2-(Vinyloxy)ethoxy)ethanol The title of the article was Decoding products of diversity pathways from stock solutions derived from single polymeric macrobeads. And the article contained the following:

A combinatorial library of nonracemic dihydropyrancarboxamides such as I [prepared on solid phase by the enantioselective Diels-Alder cycloaddition of resin-bound vinyl ethers with allyl β,γ-unsaturated-α-ketoesters in the presence of nonracemic bisoxazoline ligands and copper (II) triflate] using a novel tagging technique for the labeling and identification of members of combinatorial libraries. Chloroarom. diazoketones II (n = 1, 7, 14; R = H, Cl) were used as tagging agents to identify the sequence of reactions to which a resin bead had been subjected; treatment of a resin bead with II in the presence of dirhodium tetrakis(triphenylacetate) yielded a polystyrene resin containing a fraction of chloroaralkyl cycloheptatriene moieties (formed by ring expansion of the polystyrene Ph groups). Oxidative cleavage of the tags with ceric ammonium nitrate liberated the chloroarom. portion of the tags; treatment of the tags with N,O-bis(trimethylsilyl)acetamide and gas chromatog. yielded masses corresponding to the sequence of reactions to which beads were subjected and thus their identities. The tags could be decoded either directly from a bead before compound cleavage, from a bead after compound cleavage, or from compound stock solutions (generated by compound cleavage and dissolution of a fraction of the liberated compounds in THF/H2O). Decoding compound stock solutions was the most effective method of identifying library members; compounds were identified by tag cleavage of solutions containing 1 or 5% of the compound cleaved from a single bead. Stock solutions were decoded most effectively because a fraction of the library member on a given bead was tagged with the chloroarom. diazoketone in addition to the polystyrene resin (due to the high-loading resin used) and because oxidative cleavage of the tags with CAN proceeded more readily in solution than on solid support. A sublibrary of 108 beads chosen from the larger combinatorial library was decoded by this procedure; of the 108 compounds, 107 were successfully decoded. Four different synthetic pathways were found to be compatible with the diazoketone tagging methodol. (no data). The use of stock solutions for the decoding and deconvolution of combinatorial libraries is amenable to robotic methods for combinatorial library synthesis and testing, minimizes the storage requirements for combinatorial libraries, and allows for simpler and faster compound identification. The experimental process involved the reaction of 2-(2-(Vinyloxy)ethoxy)ethanol(cas: 929-37-3).Recommanded Product: 2-(2-(Vinyloxy)ethoxy)ethanol

The Article related to polymeric macrobead decoding stock solution, dihydropyrancarboxamide combinatorial library stereoselective enantioselective preparation, chloroarom diazoketone tag decoding identification member combinatorial library, decoding product diversity pathway stock solution polymeric macrobead, oxidative cleavage chloroarom diazoketone tag polymeric macrobead and other aspects.Recommanded Product: 2-(2-(Vinyloxy)ethoxy)ethanol

Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem