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Oxidation of Cyclic Ethers by Iodine Tris(trifluoroacetate). – Synthesis and NMR Analysis of Trifluoroacetylated Deoxypentopyranoses and of 3-Deoxy-threo-pentose

Oxidation of tetrahydro-2H-pyran (2) by iodine tris(trifluoroacetate) (1) yields the dideoxypentopyranose derivatives 3a-b and the ring-contracted compound 4.Similarly, 3-(trifluoroacetoxy)tetrahydro-2H-pyran (5) is oxidized to yield the deoxypentopyranose derivatives 6a-d and the ring-contracted compound 7.Hydrolysis of 6b yields 3-deoxy-threo-pentose 8 which is thus available in 3 or 4 steps, respectively, instead of 9 steps before.The solution of 8 in water contains the 4 ring-tautomers 8a-d. – Analysis of the 1H NMR spectra of 6a-d reveals that (a) the anomeric effect of the trifluoroacetoxy group is larger than that of the acetoxy group and (b) that the 1H signals are shifted downfield by trifluoroacetoxy groups (OX) located in gamma or even in delta position, provided that H and OX have a well-defined orientation.

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3-PHENYLPYRAZOLO[5,1-B]THIAZOLE COMPOUNDS

A compound represented by the following formula (I), or salt thereof exhibits excellent CRF receptor antagonism, and sufficient pharmacological activity, safety and pharmacokinetic properties as a drug. Wherein R1 represents the formula -A11-A12; R2 represents tetrahydrofurylmethyl, tetrahydropyranylmethyl or tetrahydropyranyl; A11 represents a single bond, methylene or 1,2-ethylene; A12 represents C1-6 alkyl, C3-6 cycloalkyl or C3-6 cycloalkyl having methyl; R3 represents methoxy, cyano, cyclobutyloxymethyl, methoxymethyl or ethoxymethyl; and R4 represents methoxy or chlorine

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Hydroboration of Prochiral Olefins with Chiral Lewis Base-Borane Complexes: Relationship to the Mechanism of Hydroboration

Alcohols with up to 19percent enantiomeric excess were obtained on hydroboration/oxidation of representative prochiral olefins using N-isobornyl-N-methylaniline-borane or N-benzyl-N-isopropyl-alpha-methylbenzylamine-borane indicating that the Lewis base is present in the hydroboration transition state.

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Tetrahydropyran – Wikipedia,
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STRUCTURE AND FORMATION OF C4H7O(1+) IONS RESULTING FROM ELECTRON IMPACT INDUCED DECOMPOSITION OF CYCLIC PRECURSORS

Possible structures and modes of formation of C4H7O(1+) ions formed by electron impact induced decomposition of tetrahydrofuran and tetrahydropyran derivates are discussed in view of labelling results and MIKE, CA, and T data.Limitations of these techniques are pointed out.

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Tetrahydropyran – Wikipedia,
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The reactant in an enzyme-catalyzed reaction is called a substrate. Enzyme inhibitors cause a decrease in the reaction rate of an enzyme-catalyzed reaction.I hope my blog about 19752-84-2 is helpful to your research., Safety of Tetrahydro-2H-pyran-3-ol

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Regiochemical control of the ring opening of 1,2-epoxides by means of chelating processes. Part 15: Regioselectivity of the opening reactions with MeOH of remote O-substituted regio- and diastereoisomeric pyranosidic epoxides under condensed- and gas-phase operating conditions

The regiochemical behavior of pairs of regio- and diastereoisomeric epoxides derived from the 3,4,5,6-tetrahydro-2H-pyrane system, bearing an acetal group as the remote functionality, was determined in the acid methanolysis in the condensed phase (cd-phase) and in the reaction with MeOH in the gas-phase using a gaseous acid (D3+), as the promoting agent. With only one exception, the results obtained in the opening process of these epoxides indicate the incursion in the gas-phase of D+-mediated chelated bidentate species able to modify the regiochemical result found in the methanolysis in the cd-phase.

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Tetrahydropyran – Wikipedia,
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Synthesis of (S)-3-hydroxytetrahydropyran from L-glutamic acid

A concise synthesis of (S)-3-hydroxytetrahydropyran from natural L-glutamic acid has been developed. The intramolecular etherification starting from 1,5-diol was promoted by trifluoromethanesulfonic anhydride. The clinnamates of the alcohols were prepared for accurately determining the optical purity by HPLC method.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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Hydroboration. 71. Hydroboration of Representative Heterocyclic Olefins with Borane-Methyl Sulfide, 9-Borabicyclo<3.3.1>nonane, Dicyclohexylborane, and Disiamylborane. Synthesis of Heterocyclic Alcohols

The hydroboration of representative heterocycles bearing an endocyclic double bond with borane-methyl sulfide (BMS), 9-borabicyclo<3.3.1>nonane (9-BBN), dicyclohexylborane (Chx2BH), and disiamylborane (Sia2BH) was investigated systematically to establish the optimum conditions for the clean and quantitative hydroboration.The hydroboration of 2,3- and 2,5-dihydrofurans with BMS (3:1 molar ratio) at 25 deg C for 1 h affords the trialkylborane, readily oxidized to 3-hydroxytetrahydrofuran in excellent yield.However, preparation of the corresponding dialkylboranes from these olefins using 2 olefin/BMS was not possible even at 0 deg C.Excess hydride and prolongated reaction time cause ring cleavage of the alkylboranes to yield both unsaturated alcohol and the dihydroborated products 1,3- and 1,4-pentanediols.Hydroboration of both 2,3-dihydrothiophene and 2-methyl-4,5-dihydrofuran with BMS proceeds cleanly to the trialkylborane stage, oxidized to the corresponding alcohols in almost quantitative yields.Hydroboration of 3-pyrroline with BMS could not be achieved with the unprotected nitrogen atom.Such hydroboration could be accomplished by protecting the nitrogen atom with the benzyloxycarbonyl group affording the trialkylborane, readily converted to N-(benzyloxycarbonyl)-3-pyrrolidinol in good yield.Conditions for a clean hydroboration of these heterocyclic five-membered olefins with 9-BBN, Chx2BH, and Sia2BH were also established.In all cases clean trialkylboranes were obtained, readily oxidized to heterocyclic alcohols in high yields. 3,4-Dihydropyran, on hydroboration with BMS, followed by oxidation, affords 3-hydroxytetrahydropyran in good yield.However, ring cleavage in this case is greater when compared to 2,3-dihydrofuran. 2-Methoxy- or 2-ethoxy-3,4-dihydro-2H-pyran readily undergo hydroboration with BMS to the trialkylboranes, oxidized to the corresponding trans and cis alcohols in a 7:3 ratio.As the steric requirements of the dialkylborane are increased, more trans alcohol is formed.Thus at 0 deg C, the ratios of trans to cis alcohols were increased from 1:1 to 7:3 and then to 8:2 with 9-BBN, Chx2BH, and Sia2BH, respectively.N-(Benzyloxycarbonyl)-1,2,3,6-tetrahydropyridine is readily hydroborated with BMS, 9-BBN, Chx2BH, and Sia2BH to the corresponding trialkylboranes, readily oxidized to N-(benzyloxycarbonyl)-3- and -4-piperidinols in good yield.Strongly basic groups in the heterocyclic ring can greatly reduce the ease of hydroboration, and the introduction of boron beta to the heteroatom can lead to elimination.However, both problems can be avoided to provide ready hydroboration-oxidation of heterocyclic olefins.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics

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19752-84-2, Children learn through play, and they learn more than adults might expect. Science experiments are a great way to spark their curiosity, get their minds active, and encourage them to do something that doesn’t involve a screen. 19752-84-2, C5H10O2. A document type is Article, introducing its new discovery.

Hydroboration. 71. Hydroboration of Representative Heterocyclic Olefins with Borane-Methyl Sulfide, 9-Borabicyclo<3.3.1>nonane, Dicyclohexylborane, and Disiamylborane. Synthesis of Heterocyclic Alcohols

The hydroboration of representative heterocycles bearing an endocyclic double bond with borane-methyl sulfide (BMS), 9-borabicyclo<3.3.1>nonane (9-BBN), dicyclohexylborane (Chx2BH), and disiamylborane (Sia2BH) was investigated systematically to establish the optimum conditions for the clean and quantitative hydroboration.The hydroboration of 2,3- and 2,5-dihydrofurans with BMS (3:1 molar ratio) at 25 deg C for 1 h affords the trialkylborane, readily oxidized to 3-hydroxytetrahydrofuran in excellent yield.However, preparation of the corresponding dialkylboranes from these olefins using 2 olefin/BMS was not possible even at 0 deg C.Excess hydride and prolongated reaction time cause ring cleavage of the alkylboranes to yield both unsaturated alcohol and the dihydroborated products 1,3- and 1,4-pentanediols.Hydroboration of both 2,3-dihydrothiophene and 2-methyl-4,5-dihydrofuran with BMS proceeds cleanly to the trialkylborane stage, oxidized to the corresponding alcohols in almost quantitative yields.Hydroboration of 3-pyrroline with BMS could not be achieved with the unprotected nitrogen atom.Such hydroboration could be accomplished by protecting the nitrogen atom with the benzyloxycarbonyl group affording the trialkylborane, readily converted to N-(benzyloxycarbonyl)-3-pyrrolidinol in good yield.Conditions for a clean hydroboration of these heterocyclic five-membered olefins with 9-BBN, Chx2BH, and Sia2BH were also established.In all cases clean trialkylboranes were obtained, readily oxidized to heterocyclic alcohols in high yields. 3,4-Dihydropyran, on hydroboration with BMS, followed by oxidation, affords 3-hydroxytetrahydropyran in good yield.However, ring cleavage in this case is greater when compared to 2,3-dihydrofuran. 2-Methoxy- or 2-ethoxy-3,4-dihydro-2H-pyran readily undergo hydroboration with BMS to the trialkylboranes, oxidized to the corresponding trans and cis alcohols in a 7:3 ratio.As the steric requirements of the dialkylborane are increased, more trans alcohol is formed.Thus at 0 deg C, the ratios of trans to cis alcohols were increased from 1:1 to 7:3 and then to 8:2 with 9-BBN, Chx2BH, and Sia2BH, respectively.N-(Benzyloxycarbonyl)-1,2,3,6-tetrahydropyridine is readily hydroborated with BMS, 9-BBN, Chx2BH, and Sia2BH to the corresponding trialkylboranes, readily oxidized to N-(benzyloxycarbonyl)-3- and -4-piperidinols in good yield.Strongly basic groups in the heterocyclic ring can greatly reduce the ease of hydroboration, and the introduction of boron beta to the heteroatom can lead to elimination.However, both problems can be avoided to provide ready hydroboration-oxidation of heterocyclic olefins.

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Tetrahydropyran – Wikipedia,
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N-methyl-N-phenyl-5-oxa-1-azaspiro[2.5]oct-1-en-2-amine – Synthesis and reactions of a synthon for AN UNKNOWN alpha-AMINO ACID

The synthesis of the heterospirocyclic amino azirine N-methyl-N-phenyl-5- oxa-1-azaspiro[2.5]oct-1-en-2-amine (6a) was achieved from 3,4-dihydro-2H-pyrane (7) via N-methyl-N-phenyltetrahydropyran-3-thiocarboxamide (11). The reactions of 6a with thiobenzoic acid and Z-Phe-OH, respectively, leading to the corresponding 3-benzoylaminotetrahydropyran-3-thiocarboxamide (13) and the diastereoisomeric dipeptide amides (14), respectively, demonstrate that 6a is a valuable synthon for the hitherto unknown 3-aminotetrahydropyrane-3-carboxylic acid. The structure of 13 was established by X-Ray crystallography. The Japan Institute of Heterocyclic Chemistry.

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Structure-based discovery of C-2 substituted imidazo-pyrrolopyridine JAK1 inhibitors with improved selectivity over JAK2

Herein we describe our successful efforts in obtaining C-2 substituted imidazo-pyrrolopyridines with improved JAK1 selectivity relative to JAK2 by targeting an amino acid residue that differs between the two isoforms (JAK1: E966; JAK2: D939). Efforts to improve cellular potency by reducing the polarity of the inhibitors are also detailed. The X-ray crystal structure of a representative inhibitor in complex with the JAK1 enzyme is also disclosed.

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Tetrahydropyran – Wikipedia,
Tetrahydropyran – an overview | ScienceDirect Topics