Category: 83435-58-9

The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Boc-D-Prolinol( cas:83435-58-9 ) is researched.Computed Properties of C10H19NO3.Kurokawa, Masayuki; Shindo, Takeyuki; Suzuki, Masumi; Nakajima, Nobuyoshi; Ishihara, Kohji; Sugai, Takeshi published the article 《Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP》 about this compound( cas:83435-58-9 ) in Tetrahedron: Asymmetry. Keywords: carbamoylmethoxymethylpyrrolidine enantiomer preparation chiral auxiliary methoxymethyl pyrrolidinamine; proline derivative kinetic resolution enzymic hydrolysis. Let’s learn more about this compound (cas:83435-58-9).

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders’ chiral auxiliaries, SAMP [(2S)-1-Pyrrolidinamine, 2-(methoxymethyl)] and RAMP [(2R)-1-Pyrrolidinamine, 2-(methoxymethyl)], enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters (Boc = tert-butoxycarbonyl, Cbz = benzyloxycarbonyl) and prolinols were examined B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E = 2.8), and in contrast, a purified protease (isoenzyme A) from the earthworm showed the preference of (S)-enantiomer (E = 13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline Me ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.

Although many compounds look similar to this compound(83435-58-9)Computed Properties of C10H19NO3, numerous studies have shown that this compound(SMILES:O=C(N1[C@@H](CO)CCC1)OC(C)(C)C), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Computed Properties of C10H19NO3. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate. Author is Kobayashi, Naotake; Sato, Norihito; Sugita, Katsuji; Takahashi, Kouji; Sugawara, Tamio; Tada, Yukio; Yoshikawa, Takayoshi.

We discovered the orally active TSH-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after i.v. (iv) administration is 100-fold higher than that of TRH. As 1 has four asym. carbons in its mol., there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure-activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Product Details of 83435-58-9. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Synthesis of enantiomerically pure nitronyl nitroxide radicals through chiral pool. Author is Qin, Xiang-Yang; Ma, Yue; Wang, Qiao-Feng; Wang, Chao; Sun, Xiao-Li; Liu, Peng.

Two pairs of new optically active nitronyl nitroxides derived from N-Boc-D- or -L-prolinol were described. The synthetic route consists of (1) the synthesis of chiral aryl aldehydes by Mitsunobu reaction, (2) condensation of 2,3-bis(hydroxylamino)-2,3-dimethylbutane with chiral aldehydes to give 1,3-dihydroxyimidazolidines, and (3) finally, subsequent oxidation with aqueous NaIO4 at 0°. These two pairs were specifically designed for further assessing the differences in activity of chiral nitronyl nitroxides and for developing chiral mol. magnetic material by the metal-radical complexes approach.

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Thiazole | C3H3NS – PubChem,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Enzyme-catalyzed enantiomeric resolution of N-Boc-proline as the key-step in an expeditious route towards RAMP, the main research direction is carbamoylmethoxymethylpyrrolidine enantiomer preparation chiral auxiliary methoxymethyl pyrrolidinamine; proline derivative kinetic resolution enzymic hydrolysis.COA of Formula: C10H19NO3.

For the preparation of both enantiomers of N-carbamoyl-2-methoxymethylpyrrolidine, the precursors of Enders’ chiral auxiliaries, SAMP [(2S)-1-Pyrrolidinamine, 2-(methoxymethyl)] and RAMP [(2R)-1-Pyrrolidinamine, 2-(methoxymethyl)], enzyme-catalyzed kinetic resolution of racemic N-carbamoyl, N-Boc, N-Cbz proline esters (Boc = tert-butoxycarbonyl, Cbz = benzyloxycarbonyl) and prolinols were examined B. licheniformis protease (subtilisin) preferentially hydrolyzed the (R)-carbamoylproline ester with an enantiomeric ratio (E) of 10. To a hydrophobic N-Cbz proline ester, subtilisin showed lower selectivity (E = 2.8), and in contrast, a purified protease (isoenzyme A) from the earthworm showed the preference of (S)-enantiomer (E = 13.6). In a practical sense, C. antarctica lipase B (Chirazyme L-2) was effective for the hydrolysis of both N-Boc and N-Cbz derivatives with E >100. The e.e. of (R)-N-carbamoyl-2-methoxymethylpyrrolidine was raised to be >99.9% by recrystallization at the N-Boc-prolinol stage, which was derived from the (R)-N-Boc-proline Me ester (98.7% e.e.) through a preparative-scale enzyme-catalyzed resolution (49% yield) of the racemic substrate.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Related Products of 83435-58-9. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Boc-D-Prolinol, is researched, Molecular C10H19NO3, CAS is 83435-58-9, about Asymmetric synthesis of (R)- and (S)-2-pyrrolidinemethanesulfonic acid. Author is Braghiroli, Daniela; Avallone, Rossella; Di Bella, Maria.

(R)- and (S)-2-Pyrrolidinemethanesulfonic acid were synthesized from the corresponding N-Boc-2-(hydroxymethyl)-1-pyrrolidine. This asym. synthesis proceeds in mild conditions, with good overall yields and high enantiomeric purities (>99% ee).

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Arnold, Kenny; Batsanov, Andrei S.; Davies, Bryan; Grosjean, Christophe; Schuetz, Thorben; Whiting, Andrew; Zawatzky, Kerstin published an article about the compound: Boc-D-Prolinol( cas:83435-58-9,SMILESS:O=C(N1[C@@H](CO)CCC1)OC(C)(C)C ).Quality Control of Boc-D-Prolinol. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:83435-58-9) through the article.

(-)-Sparteine directed lithiation of N-Boc-pyrrolidine, alkylation with chloromethylboronate pinacol ester and acid-based deprotection provides homoboroproline I HX salt in 94% ee. Salts of I are shown to be efficient enamine-type pyrrolidine catalysts in an asym. aldol reaction when neutralized, and especially when esterified in situ with a tartrate ester, for example, providing 90% ee of the aldol adduct derived from acetone and p-nitrobenzaldehyde.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Synthesis and evaluation of in vivo anti-hypothermic effect of all stereoisomers of the thyrotropin-releasing hormone mimetic: Rovatirelin Hydrate, published in 2019, which mentions a compound: 83435-58-9, mainly applied to TRH mimetic rovatirelin stereoisomers antihypothermic effect SAR; TRH; TRH mimetic; anti-hypothermic effect; intravenous administration; rovatirelin; stereoisomers, Computed Properties of C10H19NO3.

We discovered the orally active TSH-releasing hormone (TRH) mimetic: (4S,5S)-5-methyl-N-{(2S)-1-[(2R)-2-methylpyrrolidin-1-yl]-1-oxo-3-(1,3-thiazol-4-yl)propan-2-yl}-2-oxo-1,3-oxazolidine-4-carboxamide 1 (rovatirelin). The central nervous system (CNS) effect of rovatirelin after i.v. (iv) administration is 100-fold higher than that of TRH. As 1 has four asym. carbons in its mol., there are 16 stereoisomers. We synthesized and evaluated the anti-hypothermic effect of all stereoisomers of 1, which has the (4S),(5S),(2S),(2R) configuration from the N-terminus to the C-terminus, in order to clarify the structure-activity relationship (SAR) of stereoisomers. The (4R),(5R),(2R),(2S)-isomer 16 did not show any anti-hypothermic effect. Only the (4S),(5S),(2S),(2S)-isomer 10, which has the (2S)-2-methylpyrrolidine moiety at the C-terminus showed the anti-hypothermic effect similar to 1. Stereoisomers, which have the (5R) configuration of the oxazolidinone at the N-terminus and the (2R) configuration at the middle-part, showed a much lower anti-hypothermic effect than that of 1. On the other hand, stereoisomers, which have the (4R) configuration of the oxazolidinone at the N-terminus or the (2S) configuration of the C-terminus, have little influence on the anti-hypothermic effect.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica

Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 83435-58-9, is researched, SMILESS is O=C(N1[C@@H](CO)CCC1)OC(C)(C)C, Molecular C10H19NO3Journal, Article, Journal of Medicinal Chemistry called Discovery of 4-[(2S)-2-{[4-(4-Chlorophenoxy)phenoxy]methyl}-1-pyrrolidinyl]butanoic Acid (DG-051) as a Novel Leukotriene A4 Hydrolase Inhibitor of Leukotriene B4 Biosynthesis, Author is Sandanayaka, Vincent; Mamat, Bjorn; Mishra, Rama K.; Winger, Jennifer; Krohn, Michael; Zhou, Li-Ming; Keyvan, Monica; Enache, Livia; Sullins, David; Onua, Emmanuel; Zhang, Jun; Halldorsdottir, Gudrun; Sigthorsdottir, Heida; Thorlaksdottir, Audur; Sigthorsson, Gudmundur; Thorsteinnsdottir, Margret; Davies, Douglas R.; Stewart, Lance J.; Zembower, David E.; Andresson, Thorkell; Kiselyov, Alex S.; Singh, Jasbir; Gurney, Mark E., the main research direction is pyrrolidinylbutanoate preparation leukotriene hydrolase inhibitor SAR.HPLC of Formula: 83435-58-9.

Both inhouse human genetic and literature data have converged on the identification of leukotriene 4 hydrolase (LTA4H) as a key target for the treatment of cardiovascular disease. We combined fragment-based crystallog. screening with an iterative medicinal chem. effort to optimize inhibitors of LTA4H. Ligand efficiency was followed throughout our structure-activity studies. As applied within the context of LTA4H inhibitor design, the chem. team was able to design a potent compound 20 (DG-051, I) (Kd = 26 nM) with high aqueous solubility (>30 mg/mL) and high oral bioavailability (>80% across species) that is currently undergoing clin. evaluation for the treatment of myocardial infarction and stroke. The structural biol.-chem. interaction described in this paper provides a sound alternative to conventional screening techniques. This is the first example of a gene-to-clinic paradigm enabled by a fragment-based drug discovery effort.

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Thiazole | C3H3NS – PubChem,
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Dolewski, Ryan D.; Fricke, Patrick J.; McNally, Andrew published an article about the compound: Boc-D-Prolinol( cas:83435-58-9,SMILESS:O=C(N1[C@@H](CO)CCC1)OC(C)(C)C ).Name: Boc-D-Prolinol. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:83435-58-9) through the article.

Many drug fragments and therapeutic compounds contain multiple pyridines and diazines. Developing site-selective reactions where specific C-H bonds can be transformed in polyazine structures would enable rapid access to valuable derivatives Authors present a study that addresses this challenge by selectively installing a phosphonium ion as a versatile functional handle. Inherent factors that control site-selectivity are described along with mechanistically driven approaches for site-selective switching, where the C-+PPh3 group can be predictably installed at other positions in the polyazine system. Simple protocols, readily available reagents, and application to complex drug-like mols. make this approach appealing to medicinal chemists.

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Thiazole | C3H3NS – PubChem,
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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Article, ACS Catalysis called Cobalt-Catalyzed Alkylation of Drug-Like Molecules and Pharmaceuticals Using Heterocyclic Phosphonium Salts, Author is Zhang, Xuan; McNally, Andrew, which mentions a compound: 83435-58-9, SMILESS is O=C(N1[C@@H](CO)CCC1)OC(C)(C)C, Molecular C10H19NO3, Recommanded Product: Boc-D-Prolinol.

Alkylated pyridines are common in pharmaceuticals, and metal catalysis is frequently used to prepare this motif via Csp2-Csp3 coupling processes. We present a cobalt-catalyzed coupling reaction between pyridine phosphonium salts and alkylzinc reagents that can be applied to complex drug-like fragments and for late-stage functionalization of pharmaceuticals. The reaction generally proceeds at room temperature, and 4-position pyridine C-H bonds are the precursors in this strategy. Given the challenges in selectively installing (pseudo)halides in complex pyridines, this two-step process enables sets of mols. to be alkylated that would be challenging using traditional cross-coupling methods.

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Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica