125992-58-7

Upstream product

• 108-05-4 vinyl acetate 
• 51329-29-4 (+/-)-cis-2-(benzyloxy)cyclohexanol 
• 1792-81-0 cis-1,2-cyclohexane 
• 100-39-0 benzyl bromide 
• 1228121-63-8 (1S,2S)-2-benzyloxy-3-chlorocyclohex-3-en-1-ol 
• 100-44-7 benzyl chloride 
• 32700-48-4 [(cyclohex-2-en-1-yloxy)methyl]benzene 
• 84029-20-9 racemic cis-1-benzyloxy-7-oxabicyclo[4.1.0]heptane 
• 1192-78-5 2,3-epoxycyclohexanol 
• 822-67-3 Cyclohex-2-enol 

Downstream Products

• 166271-30-3 (-)-1,5-bis-<2'-(benzyloxy)cyclohexyloxy>-3-oxapentane 
• 71797-10-9 <2α,3aβ,7aβ>-2-phenylhexahydro-1,3-benzodioxole 
• 71797-11-0 <2α,3aα,7aα>-2-phenylhexahydro-1,3-benzodioxole 
• 125992-59-8 Acetic acid (1R,2S)-2-benzyloxy-cyclohexyl ester 
• 166271-29-0 C₃₀H₃₈N₄O₁₀ 
• 166376-76-7 (+)-2,2'-oxybis(ethyleneoxy)dicyclohexanol 
• 166376-75-6 C₃₀H₃₈N₄O₁₀ 
• 166376-78-9 (+)-1,5-bis-<2'-(benzyloxy)cyclohexyloxy>-3-oxapentane 
• 166376-79-0 (-)-2,2'-oxybis(ethyleneoxy)dicyclohexanol 
• 166376-77-8 (1R,2S)-2-benzyloxycyclohexan-1-ol 

Relevant academic research and scientific papers

Dimethyltin Dichloride Catalyzed Regioselective Alkylation of cis-1,2-Diols at Room Temperature

Here, we have developed a mild and general method for the regioselective installation of benzyl, allyl, para-methoxybenzyl and naphthyl groups on cis-1,2-diols. The optimized method operates at room temperature using dimethyltin dichloride as catalyst and

CDPK1 INHIBITORS, COMPOSITIONS, AND METHODS RELATED THERETO

The invention relates to inhibitors of calcium-dependent protein kinase 1 (CDPK1) and pharmaceutical preparations thereof. The invention further relates to methods of treatment of parasitic infections, such as T. gondii, P. falciparum, C. hominis, or C. parvum infections, using the novel inhibitors of the invention.

Enantioselective Desymmetrization of 2-Aryl-1,3-propanediols by Direct O-Alkylation with a Rationally Designed Chiral Hemiboronic Acid Catalyst That Mitigates Substrate Conformational Poisoning

Enantioselective desymmetrization by direct monofunctionalization of prochiral diols is a powerful strategy to prepare valuable synthetic intermediates in high optical purity. Boron acids can activate diols toward nucleophilic additions; however, the design of stable chiral catalysts remains a challenge and highlights the need to identify new chemotypes for this purpose. Herein, the discovery and optimization of a bench-stable chiral 9-hydroxy-9,10-boroxarophenanthrene catalyst is described and applied in the highly enantioselective desymmetrization of 2-aryl-1,3-diols using benzylic electrophiles under operationally simple, ambient conditions. Nucleophilic activation and discrimination of the enantiotopic hydroxy groups on the diol substrate occurs via a defined chairlike six-membered anionic complex with the hemiboronic heterocycle. The optimal binaphthyl-based catalyst 1g features a large aryloxytrityl group to effectively shield one of the two prochiral hydroxy groups on the diol complex, whereas a strategically placed "methyl blocker"on the boroxarophenanthrene unit mitigates the deleterious effect of a competing conformation of the complexed diol that compromised the overall efficiency of the desymmetrization process. This methodology affords monoalkylated products in enantiomeric ratios equal or over 95:5 for a wide range of 1,3-propanediols with various 2-aryl/heteroaryl groups.

Benzoxaborole Catalyst for Site-Selective Modification of Polyols

The site-selective modification of polyols bearing several hydroxyl groups without the use of protecting groups remains a significant challenge in synthetic chemistry. To address this problem, novel benzoxaborole derivatives were designed as efficient catalysts for the highly site-selective and protecting-group-free modification of polyols. To identify the effective substituent groups enhancing the catalytic activity and selectivity, a series of benzoxaborole catalysts 1a–k were synthesized. In-depth analysis for the substituent effect revealed that 1i–k, bearing multiple electron-withdrawing fluoro- and trifluoromethyl groups, exhibited the greatest catalytic activity and selectivity. Moreover, 1i-catalyzed benzoylation, tosylation, benzylation, and glycosylation of various cis-1,2-diol derivatives proceeded with good yield and site-selective manner.

Optimizing Pyrazolopyrimidine Inhibitors of Calcium Dependent Protein Kinase 1 for Treatment of Acute and Chronic Toxoplasmosis

Calcium dependent protein kinase 1 (CDPK1) is an essential Ser/Thr kinase that controls invasion and egress by the protozoan parasite Toxoplasma gondii. The Gly gatekeeper of CDPK1 makes it exquisitely sensitive to inhibition by small molecule 1H-pyrazolo

Regioselective, borinic acid-catalyzed monoacylation, sulfonylation and alkylation of diols and carbohydrates: Expansion of substrate scope and mechanistic studies

Synthetic and mechanistic aspects of the diarylborinic acid-catalyzed regioselective monofunctionalization of 1,2- and 1,3-diols are presented. Diarylborinic acid catalysis is shown to be an efficient and general method for monotosylation of pyranoside derivatives bearing three secondary hydroxyl groups (7 examples, 88% average yield). In addition, the scope of the selective acylation, sulfonylation, and alkylation is extended to 1,2- and 1,3-diols not derived from carbohydrates (28 examples); the efficiency, generality, and operational simplicity of this method are competitive with those of state-of-the-art protocols including the broadly applied organotin-catalyzed or -mediated reactions. Mechanistic details of the organoboron-catalyzed processes are explored using competition experiments, kinetics, and catalyst structure-activity relationships. These experiments are consistent with a mechanism in which a tetracoordinate borinate complex reacts with the electrophilic species in the turnover-limiting step of the catalytic cycle.

Synthesis and reactions of enantiopure substituted benzene cis-hexahydro-1,2-diols

Enantiopure dis-dihydro-1,2-diol metabolites, obtained from toluene dioxygenase-catalysed dis-dihydroxylation of six monosubstituted benzene substrates, have been converted to their corresponding dis-hexahydro-1,2-diol derivatives by catalytic hydrogenation via their dis-tetrahydro-1,2-diol intermediates. Optimal reaction conditions for total catalytic hydrogenation of the dis-dihydro-1,2-diols have been established using six heterogeneous catalysts. The relative and absolute configurations of the resulting benzene dis-hexahydro-1,2-diol products have been unequivocally established by X-ray crystallography and NMR spectroscopy. Methods have been developed to obtain enantiopure dis-hexahydro-1,2diol diastereoisomers, to desymmetrise a meso-cishexahydro-1,2-diol and to synthesise 2-substituted cyclohexanols. The potential of these enantiopure cyclohexanols as chiral reagents was briefly evaluated through their application in the synthesis of two enantiomerically enriched phosphine oxides from the corresponding racemic phosphine precursors.

Catalytic monoalkylation of 1,2-diols

A catalytic monoalkylation of 1,2-diols by using a weak base has been developed. Copper(II) dichloride and boronic acids are effective catalysts for activating 1,2-diols in the presence of potassium carbonate as a base. Various 1,2-diols were selectively monoalkylated with allyl-, benzyl- and alkyl- halides in DMF by choosing a suitable catalyst for each 1,2-diols.

Preparation and Enantiomer Recognition Behaviour of Azophenolic Crown Ethers containing cis-Cyclohexane-1,2-diol as a Chiral Centre

Both enentiomers of the azophenolic crown ether 1 incorporating the cis-cyclohexane-1,2-diol residue as the chiral centre have been prepared in enantiomerically pure forms and the chiral recognition behaviour towards 2-aminoethanols and ethylamines has be

Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. 8. Synthesis and ring opening reactions of cis- and trans-oxides derived from 3-benzyloxycyclohexene and 2-benzyloxy-5,6-dihydro-2H-pyran

The regiochemical outcome of the ring opening of 1,2-epoxides bearing polar remote functionalization through chelation processes assisted by metal ions, was verified in cyclic oxirane systems having the polar functionality in an allylic position to the oxirane ring. The diastereoisomeric cis/trans epoxide pairs 5,6 and 7,8 derived from 3-benzyloxycyclohexene, and 2-benzyloxy-5,6-dihydro-2H-pyran, respectively, were prepared and several of their opening reactions were studied. The regioselectivity observed largely depends on the reaction conditions (standard or metal-assisted) and, interestingly, on the nature of the nucleophile used.