Brief introduction of 21461-84-7

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The syntheses of six enantioenriched analogs representing cyclic forms of acetylcholine are reported. (S)- and (R)-N-(2-chloroethyl)-3-acetoxypiperidine and (R,R)-, (R,S)-, (S,R)-, and (S,S)-N-(2-chloropropyl)-3-acetoxypiperidine have been synthesized from (R)- or (S)-3-hydroxypiperidine in five steps. (R)- and (S)-3-hydroxypiperidine were accessed via parallel stereospecific routes from d- and l-glutamic acid, and through fractional recrystallization of diastereomeric tartranilic acid salts. (S)-N-(2-Chloroethyl)-3-acetoxypiperidine was reacted with silver perchlorate to form a spirocyclic aziridinium analog of acetylcholine as evidenced by a characteristic 1H NMR shift for the aziridinium methylene groups.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of 21461-84-7

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The present invention relates to compounds of formula (I), wherein R1 to R5 are as described herein, and their prodrugs or pharmaceutically acceptable salt, enantiomer or diastereomer thereof, and compositions including the compounds and methods of using the compounds.

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Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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Disclosed is a method for producing integrin inhibitors of formula (I), wherein R1, R2, R3, R4, R5, and X have the meanings indicated in claim 1, and intermediate compounds.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Archives for Chemistry Experiments of 21461-84-7

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A new kind of acid sensitive tetrahydrofuranyl (THF) linker was synthesized and then reacted with 5-(6)-carboxytetramethylrhodaminesuccinimidyl ester (5(6)-TAMRA, SE), followed by di(N-succinimidyl) carbonate (DSC) and modified 2?-deoxyuridine triphosphate (dUTP); the final product, as a reversible terminator for DNA sequencing by synthesis (DNA SBS), was given obtained and confirmed by 1H-NMR, 31P-NMR, and HRMS with purity of up to 99%. The synthesized dye-labeled terminator incorporated into DNA strand successfully, and the fluorophore was cleaved completely under acidic conditions. The preliminary results encourage us to explore more acid-sensitive linkers for DNA SBS to increase the cleavage efficiency under weakly acidic conditions.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Brief introduction of (S)-( )-5-Oxo-2-tetrahydrofurancarboxylic Acid

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The propionate of (2R,8R)-8-methyl-2-decanol, (2R,8R)-1, an attractant of the western corn rootworm, Diabrotica virgifera Le Conte, has been prepared by a synthetic route in which enantiomerically pure methyl hydrogen (R)-3-methylglutarate, (R)-2, and (S)-glutamic acid, (S)-3, have been used as chiral precursors.In this convergent synthesis, (R)-2 and (S)-3 have been stereospecifically converted into (R)-1-bromo-3-methylpentane, (R)-4, and (R)-1,4-pentanediol, (R)-5, respectively.An analogous synthetic scheme has been followed to prepare biologically active (2RS, 8R)-1 starting from (R)-4 and racemic 5.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

More research is needed about (S)-( )-5-Oxo-2-tetrahydrofurancarboxylic Acid

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The invention provides compounds of general formula (I). The compounds have hemoregulatory activities and can be used to stimulate haematopoiesis and for the prevention and treatment of viral, fungal and bacterial infectious diseases. STR1

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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This invention provides compounds, methods and compositions for the treatment of inflammatory diseases, comprising the timely administration of a provided compound, which has a structure related to an endogenously formed lipid mediator. One embodiment of the present invention is directed to a compound selected from a group having the general formula A.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Discovery of 21461-84-7

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The invention relates to the technology of organic synthesis, in particular relates to a high-selective synthesis of chiral center tetrahydrofuran ring method, its mild condition, the reaction step is simple, easy to operate, regional high selectivity, high stereoselectivity; comprising the following steps: (a) glutamic acid to L – 1 as the starting material, the role of the nitride and the purified […], shall lactone intermediate 2; (b) lactone intermediate 2 by carboxyl in the reduction, to produce an intermediate 3; (c) intermediate 3 in hydroxy by TBS protection, to produce an intermediate 4; (d) the intermediate 4, substituted reaction, to produce an intermediate 5; (e) to the intermediate 5 to carry out the reduction reaction, to obtain the intermediate 6 of precursor compounds; (f) the intermediate 6 by the Wittig reaction of precursor compounds, to produce an intermediate 6; (g) intermediate 6, by the Mitsunobu reaction, to produce an intermediate 7; (h) intermediate 7, by alkali-protecting group under the action of the base and the ring, to obtain the target product 8. (by machine translation)

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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It is well recognized that carbon chirality plays a critical role in the design of drug molecules. However, very little information is available regarding the effect of stereoisomerism of macrocyclic bifunctional chelators (BFC) on biological behaviors of the corresponding radiopharmaceuticals. To evaluate such effects, three enantiopure stereoisomers of a copper radiopharmaceutical BFC bearing two chiral carbon atoms were synthesized in forms of R,R-, S,S-, and R,S-. Their corresponding peptide conjugates were prepared by coupling with a model peptide sequence, c(RGDyK), which targets the alphavbeta3 integrin for in vitro and in vivo evaluation of their biological behaviors as compared to the racemic conjugate. Despite the chirality differences, all the conjugates showed a similar in vitro binding affinity profile to the alphavbeta3 integrin (106, 108, 85 and 100 nM for rac-H2-1, RR-H2-1, SS-H 2-1, and RS-H2-1 respectively with all p values > 0.05) and a similar level of in vivo tumor uptake (2.72 ± 0.45, 2.60 ± 0.52, 2.45 ± 0.48 and 2.88 ± 0.59 for rac-64Cu-1, RR-64Cu-1, SS-64Cu-1, and RS-64Cu-1 at 1 h p.i. respectively). Furthermore, they demonstrated a nearly identical biodistribution pattern in major organs (e.g. 2.07 ± 0.21, 2.13 ± 0.58, 1.70 ± 0.20 and 1.90 ± 0.46 %ID/g at 24 h p.i. in liver for rac-64Cu-1, RR-64Cu-1, SS-64Cu-1, and RS- 64Cu-1 respectively; 1.80 ± 0.46, 2.30 ± 1.49, 1.73 ± 0.31 and 2.23 ± 0.71 at 24 h p.i. in kidneys for rac- 64Cu-1, RR-64Cu-1, SS-64Cu-1, and RS- 64Cu-1 respectively). Therefore we conclude that the chirality of BFC plays a negligible role in alphavbeta3-targeted copper radiopharmaceuticals. However, we believe it is still worthwhile to consider the chirality effects of BFCs on other targeted imaging or therapeutic agents.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem

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The highly stereocontrolled total synthesis of (-)-N-methylwelwitindolinone C isothiocyanate is described, which features the expeditious construction of a bicyclo[4.3.1]decane ring system by a palladium-catalyzed tandem enolate allylation/arylation reaction.

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Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem