Category: 58081-05-3

Formula: C4H6O3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Synthesis, X-ray Analysis, and Biological Evaluation of a New Class of Stereopure Lactam-Based HIV-1 Protease Inhibitors. Author is Wu, Xiongyu; Oehrngren, Per; Joshi, Advait A.; Trejos, Alejandro; Persson, Magnus; Arvela, Riina K.; Wallberg, Hans; Vrang, Lotta; Rosenquist, Aasa; Samuelsson, Bertil B.; Unge, Johan; Larhed, Mats.

In an effort to identify a new class of druglike HIV-1 protease inhibitors, stereopure β-hydroxy γ-lactam-containing inhibitors I (X = CH2, CH2CH2; R = H, Br, 2-pyridyl, 3-pyridyl, 4-pyridyl) have been synthesized and biol. evaluated. Three of these compounds were also cocrystd. with HIV-1 protease. The impact of the tether length of the central spacer (two or three carbons) was investigated. The compound I (X = CH2; R = Br) with a shorter tether and (3R,4S) absolute configuration exhibited high activity with a Ki of 2.1 nM and an EC50 of 0.64 μM. Further optimization by decoration of the P1′ side chain furnished an even more potent HIV-1 protease inhibitor (3R,4S)-I (X = CH2; R = 3-pyridyl) (Ki = 0.8 nM, EC50 = 0.04 μM). According to X-ray anal., this new class of inhibitors did not fully succeed in forming two sym. hydrogen bonds to the catalytic aspartates. The crystal structures of the complexes further explain the difference in potency between the shorter inhibitors (two-carbon spacer) and the longer inhibitors (three-carbon spacer).

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Name: (R)-4-Hydroxydihydrofuran-2(3H)-one. 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: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Magnesium ethoxide mediated lactone aminolysis with aminoheterocycles. Author is Mercado-Marin, Eduardo V.; Chheda, Pratik Rajesh; Faulkner, Andrea; Carrera, Diane.

A mild method for the aminolysis of lactones with aminoheterocycles in the presence of magnesium ethoxide was described. A wide range of electronically diverse aminoheterocycles and substituted lactones successfully participated in this transformation to furnish the resulting amido-alc. products. Further application of this method to the synthesis of chiral α-amino amides derivatives was also described.

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Pyrroline – Wikipedia,
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Name: (R)-4-Hydroxydihydrofuran-2(3H)-one. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Total Synthesis of (+)-Mycotrienol and (+)-Mycotrienin I: Application of Asymmetric Crotylsilane Bond Constructions.

A highly convergent asym. synthesis of the ansamycin antibiotics (+)-mycotrienin I (I) [R = 2-(S)-cyclohexylcarbonylaminopropionyl] and (+)-mycotrienol I (R = H) has been achieved through the synthesis and coupling of the C9-C16 subunit II and the aromatic subunit III, resp. This article describes the complete details of that work as it illustrates the utility of our developing chiral (E)-crotylsilane bond construction methodol. in total synthesis. All four stereogenic centers were introduced using chiral allylsilane bond construction methodol. In the synthesis of subunit II, the C12 and C13 stereocenters were installed using an asym. crotylsilylation reaction to α-keto dibenzyl acetal MeCOCH(OCH2Ph)2. The C11 stereocenter was subsequently installed via a chelate-controlled addition of allyltrimethylsilane to establish the anti-1,3-diol system. The C14-C15 trisubstituted double bond was then installed via a reductive opening of α,β-unsaturated lactone (IV). Aromatic subunit III was chosen on the basis of its synthon equivalency to the amidobenzoquinone system of I. Subunit III was constructed in a concise six-step sequence which incorporates the C3 stereogenic center of the C1-C5 side chain. The C3 stereogenic center was established using a Weinreb amidation of 2,5-dimethoxy-3-phenylsulfonylmethylaniline with (+)-3R-methoxybutanolide, whose absolute stereochem. was derived using the crotylsilane methodol. The union of subunit II with aromatic subunit III was accomplished using a sulfone-based coupling strategy. Coupling product (V) was transformed through a sequence of steps to triene. Divergence from this advanced intermediate allows access to both natural products. The successful completion of the synthesis included the incorporation of the (E,E,E)-triene unit with simultaneous macrocyclization through a palladium (0)-catalyzed (Stille-type) coupling macrocyclization.

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Reference:
Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

The three-dimensional configuration of the ester heterocycle is basically the same as that of the carbocycle. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one(SMILESS: O=C1OC[C@H](O)C1,cas:58081-05-3) is researched.Reference of 4-Methoxypiperidine. The article 《Absolute stereochemistries of the aplysiatoxins and oscillatoxin A》 in relation to this compound, is published in Journal of Organic Chemistry. Let’s take a look at the latest research on this compound (cas:58081-05-3).

CD and proton NMR spectral studies of the aplysiatoxins and derivatives, degradation products of the toxins, and an X-ray crystallog. anal. of 19,21-dibromoaplysiatoxin show that the absolute configurations of the ten asym. carbons are 3S,4R,7S,9S,10S,11R,12S,15S,29R,30R. The 31-nor compound, oscillatoxin A, has the same absolute stereochem. at C(3), C(4), C(7), C(9), C(10), C(11), C(12), C(15), and C(29).

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Pyrroline – Wikipedia,
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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 58081-05-3, is researched, Molecular C4H6O3, about Synthesis of (S)- and (R)-3-hydroxy-4-butanolide and (2S,4S)-, (2R,4S)-, (2S,4R)-, and (2R,4R)-2-hydroxy-4-(hydroxymethyl)-4-butanolide and their satiety and hunger modulating activities, the main research direction is hydroxybutanolide preparation appetite depressant; butanolide hydroxymethyl hydroxy appetite stimulant; hunger modulator hydroxybutanolide.Recommanded Product: 58081-05-3.

Two endogenous γ-lactones, 3-hydroxy-4-butanolide (I) and 2-hydroxy-4-hydrtoxymethyl-4-butanolide (II) have been identified as substances that enhance, resp., satiety and hunger by their effects on the feeding behavior and the central neurons of rats. All the stereoisomers of these two lactones were synthesized and their effects on the feeding behavior and humoral factors were assessed by infusion into the rat third cerebroventricle. Among four isomers, (2S,4S)-II was most effective in eliciting the feeding and caused potent hypoglycemia with hyperinsulinemia. (S)-I suppressed the food intake more potently than the antipode and caused humoral responses reciprocal to those of (2S,4S)-II. Thus, (S)-I and (2S,4S)-II are physiol. active forms for conveying intrinsic signals of satiety and hunger to neurons in the hypothalamus.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Product Details of 58081-05-3. 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: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Pharmacologically active compounds in the Anoectochilus and Goodyera species. Author is Du, Xiao-Ming; Irino, Nobuto; Furusho, Norihiro; Hayashi, Jun; Shoyama, Yukihiro.

The extract of Anoectochilus formosanus showed significant activity in decreasing the levels of the cytosolic enzymes LDH, GOT, and GPT, and the result demonstrated that A. formosanus possessed prominent hepatoprotective activity against CCl4-induced hepatotoxicity. Moreover, in the results of the test using aurothioglucose-induced obese mice, the extract showed a significant antihyperliposis effect. A. formosanus grown in the wild and propagated by tissue culture contain ten compounds, including a major known component, (3R)-3-(β-D-glucopyranosyloxy)butanolide (kinsenoside; 1), and two new components, (3R)-3-(β-D-glucopyranosyloxy)-4-hydroxybutanoic acid (2) and 2-[(β-D-glucopyranosyl-oxy)methyl]-5-hydroxymethylfuran (3), along with the known compounds, isopropyl-β-D-glucopyranoside (4), (R)-3,4-dihydroxybutanoic acid γ-lactone (5), 4-(β-D-glucopyranosyloxy) benzyl alc. (6), (6R,9S)-9-(β-D-glucopyranosyloxy)megastigma-4,7-dien-3-one (7), and (3R)-3-(β-D-glucopyranosyloxy)-4-hydroxybutanolide (8). Since a higher concentration of kinsenoside (1) was detected in the crude drugs A. formosanus and A. koshunensis by high-performance liquid chromatog. (HPLC) anal., we proved a simple purification system for kinsenoside (1), giving 180 mg of kinsenoside (1) from 1 g of dried samples for further pharmacol. experiments In an anti-hyperliposis assay using high-fat-diet rats, 1 significantly reduced the weights of the body and the liver, and also decreased the triglyceride level in the liver compared to those of control rats. On the other hand, the epimer of 1, (3S)3-(β-D-glucopyranosyloxy)butanolide, goodyeroside A (9), which was isolated from the Goodyera species, had no effect for anti-hyperliposis. In aurothioglucose-induced obese mice, 1 suppressed the body and liver weight increase, significantly ameliorated the triglyceride level in the liver, and also reduced the deposition of uterine fat pads. The anti-hepatoxic activities of 9 and goodyerosides B (10) were studied on injury induced by CCl4 in primary cultured rat hepatocytes by measuring the levels of LDH, GOT, and GPT. In the CCl4-treated control group, there were marked increases in LDH, GOT, and GPT activities compared with the normal group. In contrast, these levels were suppressed in 9- and 10-treated groups. Goodyerin (11), a new typical flavone glycoside, exhibited a significant and dose-dependent sedative and anticonvulsant effect.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Total synthesis of (+)-phrymarolin I from (+)-malic acid, the main research direction is phrymarolin I stereoselective total synthesis; furofuran ring system; lignan insecticidal haedoxan preparation.Electric Literature of C4H6O3.

(+)-Phrymarolin I (I) was stereoselectively synthesized from (R)-(+)-3-hydroxybutanolide that had been prepared via regioselective reduction of (+)-malic acid or microbial reduction of 4-tert-butoxyacetoacetate. The procedure is more efficient than the previous synthesis in terms of fewer reaction steps and the easier availability of the starting material.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

Recommanded Product: (R)-4-Hydroxydihydrofuran-2(3H)-one. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Glycosidic constituents from in vitro Anoectochilus formosanus.

The glycosidic constituents of whole plants of Anoectochilus formosanus propagated by tissue culture were investigated. A new compound, 2-(β-D-glucopyranosyloxymethyl)-5-hydroxymethylfuran, along with the known compounds, 3-(R)-3-β-D-glucopyranosyloxybutanolide (kinsenoside), 3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid, 1-O-isopropyl-β-D-glucopyranoside, (R)-(+)-3,4-dihydroxybutanoic acid γ-lactone, 4-(β-D-glucopyranosyloxy)benzyl alc., (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside, and corchoionoside C were isolated.

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Pyrroline – Wikipedia,
1-Pyrroline | C4H7N – PubChem

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, Tetrahedron called Enantiomerically pure β,γ-epoxyesters from β-hydroxylactones: synthesis of β-hydroxyesters and (-)-GABOB, Author is Larcheveque, M.; Henrot, S., which mentions a compound: 58081-05-3, SMILESS is O=C1OC[C@H](O)C1, Molecular C4H6O3, Safety of (R)-4-Hydroxydihydrofuran-2(3H)-one.

The preparation of enantiomerically pure β,γ-epoxy esters was achieved by chemoselective opening of β-hydroxybutanolides with Me3SiI followed by cyclization of the resulting iodohydrins with Ag2O. The reaction of these epoxy esters with lithio- or magnesiocuprates afforded stereochemically pure α-substituted-β-hydroxy esters. Alternatively, the title compound, (R)-H2NCH2CH(OH)CH2CO2H, was synthesized in optically pure form from the iodohydrin (R)-ICH2CH(OH)CH2CO2Et.

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Pyrroline – Wikipedia,
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The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (R)-4-Hydroxydihydrofuran-2(3H)-one, is researched, Molecular C4H6O3, CAS is 58081-05-3, about Synthesis of a new cerebroside isolated from Typhonium giganteum Engl, the main research direction is typhoniside cerebroside asym preparation; sn2 nucleophilic substitution typhoniside preparation.Related Products of 58081-05-3.

The stereoselective synthesis of typhoniside, a new cerebroside isolated from Typhonium giganteum Engl. was accomplished. Cerebrosides are a kind of glycolipids highly enriched on the surface of myelin-producing cells and are composed by C18-4, 8-sphingadienine, α-hydroxy acid and a saccharide head. In this paper, C18-4, 8-sphingadienine was synthesized from D-xylose via a SN2 type reaction. α-Hydroxy acid was prepared from (R)-4-hydroxyte-trahydrofuran-2-one, which in turn could be obtained from L-ascorbic acid.

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Reference:
Pyrroline – Wikipedia,
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