110716-78-4

Upstream product

• 286-20-4 cyclohexane-1,2-epoxide 
• 260260-97-7 (+)-(1R,2R)-2-azidocyclohexyl acetate 
• 123-62-6 propionic acid anhydride 
• 13374-31-7 (1R,2R)-trans-2-aminocyclohexanol hydrochloride 
• 108-05-4 vinyl acetate 

Downstream Products

• 1439909-20-2 (1R,2R)-2-ethoxycyclohexanamine 
• 1439905-65-3 4-(3-(2H-1,2,3-triazol-2-yl)phenylamino)-2-((1R,2R)-2-ethoxycyclohexylamino)pyrimidin-5-carboxamide 
• 1439909-19-9 C₈H₁₅N₃O 
• 178272-03-2 (S)-N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-3-tert-butoxycarbonylamino-succinamic acid benzyl ester 
• 182265-22-1 4-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propylcarbamoyl}-butyric acid benzyl ester 
• 182265-23-2 N-{(1S,2S)-3-Benzyloxy-2-hydroxy-1-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-propyl}-succinamic acid benzyl ester 
• 178272-07-6 {(4aR,6R,8R,8aR)-6-Methoxy-2-phenyl-6-[(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy}-acetic acid methyl ester 
• 178272-06-5 (4aR,6R,8R,8aR)-8-Hydroxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-6-carboxylic acid [(1R,2R)-2-((2R,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexyl]-amide 
• 189071-51-0 {(2R,4R,5R,6R)-5-Hydroxy-6-hydroxymethyl-2-methoxy-2-[(1R,2R)-2-((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-cyclohexylcarbamoyl]-tetrahydro-pyran-4-yloxy}-acetic acid methyl ester 

Relevant academic research and scientific papers

MCM-41 bound dibenzo-18-crown-6 ether: a recoverable phase-transfer nano catalyst for smooth and regioselective conversion of oxiranes to β-azidohydrins and β-cyanohydrins in water

A new organic-inorganic hybrid nanocomposite was prepared by immobilizing dibenzo-18-crown-6 onto covalently linked amine functionalized mesoporous MCM-41 via a simple post-synthesis method. The heterogeneous hybrid nanocomposite was characterized by TEM,

Cr(salen) catalysed asymmetric ring opening reactions of epoxides in room temperature ionic liquids

Cr(salen) catalysed asymmetric ring opening reactions of epoxides with TMSN3 proceed readily in the room temperature ionic liquid 1-butyl-3-methylimidazolium salts ([bmim][X]) with easy catalyst/solvent recycling.

A new chiral titanium species for the ring opening reactions of meso epoxides

The synthesis of a new chiral ligand 1 based on the conformationally defined 1,7-dioxaspiro[5.5]undecane ring system is reported. Generation of the corresponding ligand 1-Ti(OiPr)4 complex as a catalyst and its use in the enantioselective ring

Synthesis and evaluation of new 1,7-dioxaspiro[5.5]undecane ligands: Implications for the use of diols in the desymmetrization of meso epoxides

The synthesis and preliminary evaluation of two new chiral 1,7- dioxaspiro[5.5]undecane ligands is described. The compounds of interest are readily available in enantiomerically pure form. Chiral organotitanium complexes prepared from these ligands cataly

Multigram-scale enzymatic kinetic resolution of trans-2-azidocyclohexyl acetate and chiral reversed-phase HPLC analysis of trans-2-azidocyclohexanol

Lipase-catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram-scale hydrolytic kinetic resolution of trans-2-azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative-scale process: temperature, organic co-solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc-Cl) derivatization protocol for 2-azidocyclohexanol, which enabled chiral reversed-phase high-performance liquid chromatography (RP-HPLC) determination of enantiomeric excess.

Molecular probe derived from calcium-sensitive receptor protein antagonist and application of molecular probe in parathyroid gland resection surgery

The invention discloses a molecular probe derived from a calcium-sensitive receptor protein antagonist and application of the molecular probe in parathyroid gland resection surgery. The molecular probe is specifically a molecular probe which is derived fr

HheG, a halohydrin dehalogenase with activity on cyclic epoxides

Halohydrin dehalogenases (HHDHs) are of biotechnological interest due to their promiscuous epoxide ring-opening activity with a set of negatively charged nucleophiles, enabling the formation of C-C, C-N, or C-O bonds. The recent discovery of HHDH-specific sequence motifs aided the identification of a large number of halohydrin dehalogenases from public sequence databases, enlarging the biocatalytic toolbox substantially. During the characterization of 17 representatives of these phylogenetically diverse enzymes, one HHDH, namely HheG from Ilumatobacter coccineus, was identified to convert cyclic epoxide substrates. The enzyme exhibits significant activity in the azidolysis of cyclohexene oxide and limonene oxide with turnover numbers of 7.8 and 44 s-1, respectively. As observed for other HHDHs, the cyanide-mediated epoxide ring-opening proceeded with lower rates. Wild-type HheG displays modest enantioselectivity, as the resulting azido- and cyanoalcohols of cyclohexene oxide ring-opening were obtained in 40% enantiomeric excess. These biocatalytic findings were further complemented by the crystal structure of the enzyme refined to 2.3 ?. Analysis of HheG's structure revealed a large open cleft harboring the active site. This is in sharp contrast to other known HHDH structures and aids in explaining the special substrate scope of HheG.

Stereoselective synthesis of 1,2,3-triazolooxazine and fused 1,2,3-triazolo-d-lactone derivatives

The stereoselective synthesis of 1,2,3-triazolooxazine and fused 1,2,3-triazolo-d-lactone by applying chemoenzymatic methods is described. trans-2-Azidocyclohexanol was successfully resolved by Novozyme 435 with an ee value of 99%. Installation of the alkyne moiety on the enantiomerically enriched azidoalcohol by O-alkylation, followed by intramolecular azide-alkyne [3+2] cycloaddition resulted in the desired 1,2,3-triazolooxazine derivative. Enantiomerically pure azidocyclohexanol was also subjected to the Huisgen 1,3-dipolar cycloaddition reaction with dimethylacetylene dicarboxylate, followed by intramolecular cyclization of the corresponding cycloadduct, to furnish a fused 1,2,3-triazolod-λ-lactone.

SELECTIVE KINASE INHIBITORS

Provided are pyrimidine compounds for inhibiting of Syk kinase, intermediates used in making such compounds, methods for their preparation, pharmaceutical compositions thereof, methods for inhibition Syk kinase activity, and methods for treating conditions mediated at least in part by Syk kinase activity.

Polyolefin-supported recoverable/reusable Cr(III)-salen catalysts

The design of functional soluble polyolefins for use as supports for salen ligands and metal complexes is described. Examples and applications that use both polyisobutylene (PIB)-and polyethylene (PEOlig)-bound recoverable/recyclable salen ligands/metal complexes are detailed. In the case of using PIB as a support, the polymer-bound complexes can be recovered through the use of latent biphasic or a thermomorphic mixed solvent systems. In the case of PEOlig-supported complexes, the thermomorphic PE Olig-bound salen species can be dissolved in "hot" solvents and quantitatively recovered as solids upon cooling to room temperature. Both the PIB-and PEOlig-bound salen catalysts were shown to catalyze the ring-opening of epoxides with various nucleophiles. Both sorts of polyolefin-bound catalysts can be recycled and reused with no observed loss in activity. However, limitations of catalyst concentration make chiral versions of these complexes uncompetitive in comparison to conventional chiral salen catalysts that can be used in neat substrate at higher concentration to produce high enantioselectivity in the ring-opening products. The preparation of a PIB-bound "half-salen" catalyst was also briefly examined.