Category: 32780-06-6

Reference of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one. The fused heterocycle is formed by combining a benzene ring with a single heterocycle, or two or more single heterocycles. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. 2′,3′-Dideoxy pyrimidine C-nucleosides by palladium-mediated glycal-aglycon coupling. Author is Zhang, Han Cheng; Daves, G. Doyle Jr..

Newly available enantiomeric 2,3-dideoxyglycals, (5S)- and (5R)-4,5-dihydro-5-[(triphenylmethoxy)methyl]furans and 2,4-dimethoxy-5-iodopyrimidine undergo palladium-mediated coupling by two different, complementary procedures to form enantiomeric pairs of (2′,3′-dideoxy-2′,3′-didehydrofuranosyl)- and (2′,3′-dideoxy-3′,4′-didehydrofuranosyl)pyrimidine C-nucleosides. Stereoselective reductions of the carbohydrate unsaturations produce all four enantio- and diastereoisomers of 2,4-dimethoxy-5-(2,3-dideoxy-5-O-tritylribofuranosyl)pyrimidine. The facile two-step syntheses of 2′,3′-deoxy C-nucleosides which involves preparation of a D-series C-nucleoside from an L-series glycal (and vice versa) represents a new strategy for C-nucleoside synthesis.

Different reactions of this compound((S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one)Reference of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one require different conditions, so the reaction conditions are very important.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Electric Literature of C5H8O3. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Total synthesis of (10ξ,15R,16S,19S,20S,34R)-corossoline. Author is Yao, Zhujun; Wu, Yulin.

(10ξ,15R,16S,19S,20S,34R)-corossoline (I), a structural representative of the cytotoxic monotetrahydrofuranyl annonaceous acetogenins, was synthesized from two chiral starting materials, (S)-glutamic acid and (R)-Et lactate, and 10-undecenoic acid.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Electric Literature of C5H8O3. 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: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Multi-Gram Scale Synthesis of Chiral 3-Methyl-2,5-trans-tetrahydrofurans. Author is Qin, Shuanglin; Cao, Yuting; Luo, Yunhao; Jiang, Shende; Clark, J. Stephen; Wang, Xiaoji; Yang, Guang.

In this article, we report the rapid and facile synthesis of chiral 3-methyl-2,5-trans-tetrahydrofurans. This reaction utilizes cheap and easily available starting materials. A domino hydrolysis and intramol. Michael-type ring closure reaction was the key step. As a result, synthesis of the desired 3-methyl-2,5-trans-tetrahydrofurans could be achieved in gram-scale over seven linear steps with high chem. yield and high diastereoselectivity.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Epoxy compounds usually have stronger nucleophilic ability, because the alkyl group on the oxygen atom makes the bond angle smaller, which makes the lone pair of electrons react more dissimilarly with the electron-deficient system. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about An Enantioselective Ring Expansion Route Leading to Furanose and Pyranose Nucleosides Featuring Spirodiketopiperazines at the Anomeric Position.Recommanded Product: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one.

A study directed at the enantioselective synthesis of spirodiketopiperazine homologs, e.g. I, of hydantocidin is described. Furanoid glycals, systems that are amenable to C-5 metalation in the presence of tert-butyllithium, are readily coupled to N-protected 2,3-azetidinediones provided that at least 1 equiv of BF3·OEt2 is present to curb enolization. The resulting 1:1 mixtures of carbinols undergo smooth ring expansion to spirocyclic keto amides when heated with pyridinium p-toluenesulfonate in benzene. 1,2-acyl shifts operate exclusively. Since attempts to engage these products in Beckmann rearrangement proved singularly unsuccessful, recourse was alternatively made to new methodol. based upon sequential Baeyer-Villiger oxidation and ammonolysis. The data show that the first of these steps occurs with exclusive migration of the quaternary carbon. Furthermore, nucleophilic attack by NH3 can be directed regioselectively to the anomeric region. If heating is supplied during acid-promoted cyclization to the spirodiketopiperazines, spiropyranose derivatives are produced in a complementary process. The central issue of this synthesis effort was the utilization of 4-phenylseleno-substituted furanoid glycals so as to ultimately enable introduction of the cis-diol functionality at C-3 and C-4 (hydantocidin numbering).

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Studies on structurally simple α,β-butenolides. II. (-)-(S)-γ-Hydroxymethyl-α,β-butenolide and derivatives from D-ribonolactone. Efficient synthesis of (-)-ranunculin, the main research direction is ribonolactone ethoxymethylene elimination; ranunculin total synthesis; butenolide hydroxymethyl preparation functionalization; condensation hydroxymethylbutenolide glucopyranosyl bromide; elimination ethoxymethyleneribonolactone.Application In Synthesis of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one.

Acid-catalyzed cyclocondensation reaction of D-ribonolactone with (EtO)3CH in refluxing THF for 12 h followed by pyrolysis at 220° and 40 Torr gave 68% of the title butenolide (I; R = H) (II). The preparation of chiral derivatives of II, e.g. I (R = Me, PhCH2, Bu, Ph3C, Ac), is described. Condensation reaction of II with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide in CHCl3 with stirring at room temp for 86 h gave 77% I (R = Q, R1 = Ac) which underwent deacetylation to give 85% (-)-ranunculin (I; R = Q, R1 = H).

After consulting a lot of data, we found that this compound(32780-06-6)Application In Synthesis of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Name: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Synthesis of Reblastatin, Autolytimycin, and Non-Benzoquinone Analogues: Potent Inhibitors of Heat Shock Protein 90. Author is Wrona, Iwona E.; Gozman, Alexander; Taldone, Tony; Chiosis, Gabriela; Panek, James S..

The heat shock protein 90-inhibiting natural ansamycin natural products reblastatin I (R = MeO; R1 = H; X = CH2CH2) and autolytimycin I (R = R1 = H; X = CH2CH2), and four of their analogs I [R = MeO; R1 = H, MeOCH2, H2NHCO; X = (Z)-CH:CH, CH2CH2] lacking a quinone moiety are prepared using the chemoselective, regioselective, and stereoselective zirconium-mediated coupling reaction of a methyl-substituted alkyne with an aldehyde to give an (E)-trisubstituted allylic alc. and the copper-catalyzed macroamidation reaction of terminal amides containing a bromoarene as the key steps. The competitive binding of Hsp90α to I [R = H, MeO; R1 = H, MeOCH2, H2NHCO; X = (Z)-CH:CH, CH2CH2], an uncyclized derivative of reblastatin, a reblastatin analog lacking the carbamate ester, geldanamycin, and 17-(allylamino)-17-demethoxygeldanamycin is determined; the inhibition of human myeloid leukemia cells by I [R = MeO; R1 = H, MeOCH2, H2NHCO; X = (Z)-CH:CH, CH2CH2] and by 17-(allylamino)-17-demethoxygeldanamycin (II), a geldanamycin derivative currently under evaluation for treatment of cancer, are determined Reblastatin and autolytimycin I (R = MeO, H; R1 = H; X = CH2CH2) bind heat shock protein 90 with better affinities (26 nM and 36 nM, resp.) than II (110 nM); I (R = MeO, H; R1 = H; X = CH2CH2) are more effective at inhibiting one of the human myeloid leukemia cell lines (Kasumi-1) than II but are less effective than II at inhibiting the other (MOLM-13).

The article 《Synthesis of Reblastatin, Autolytimycin, and Non-Benzoquinone Analogues: Potent Inhibitors of Heat Shock Protein 90》 also mentions many details about this compound(32780-06-6)Name: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, you can pay attention to it, because details determine success or failure

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

Recommanded Product: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, is researched, Molecular C5H8O3, CAS is 32780-06-6, about Drug delivery by an enzyme-mediated cyclization of a lipid prodrug with unique bilayer-formation properties. Author is Linderoth, Lars; Peters, Guenther H.; Madsen, Robert; Andresen, Thomas L..

Liposomal drug-delivery systems in which prodrugs are activated specifically by disease-associated enzymes have great potential for the treatment of severe diseases, such as cancer. A new type of phospholipid-based prodrug has the ability to form stable small unilamellar vesicles. Activation of the prodrug vesicles by the enzyme sPLA2 initiates a cyclization reaction, which leads to the release of the drug.

After consulting a lot of data, we found that this compound(32780-06-6)Recommanded Product: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one can be used in many types of reactions. And in most cases, this compound has more advantages.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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.Peru, Aurelien A. M.; Flourat, Amandine L.; Gunawan, Christian; Raverty, Warwick; Jevric, Martyn; Greatrex, Ben W.; Allais, Florent researched the compound: (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one( cas:32780-06-6 ).Formula: C5H8O3.They published the article 《Chemo-enzymatic synthesis of chiral epoxides ethyl and methyl (S)-3-(oxiran-2-yl)propanoates from renewable levoglucosenone: an access to enantiopure (S)-dairy lactone》 about this compound( cas:32780-06-6 ) in Molecules. Keywords: levoglucosenone Baeyer Villiger oxidation acid hydrolysis hydrogenation; butyrolactone preparation green chem; octenyl tetrahydrofuranone preparation green chem; chirality; epoxide; flavor; levoglucosenone; total synthesis. We’ll tell you more about this compound (cas:32780-06-6).

Herein, starting from levoglucosenone (LGO), a biobased chiral compound was obtained through the flash pyrolysis of acidified cellulose, a safer and more sustainable chemo-enzymic synthetic pathway involving lipase-mediated Baeyer-Villiger oxidation, palladium-catalyzed hydrogenation, tosylation and treatment with sodium ethoxide/methoxide as key steps was proposed. This route afforded Et and Me (S)-3-(oxiran-2-yl)propanoates in 57% overall yield, resp. To demonstrate the potentiality of this new synthetic pathway from LGO, the synthesis of high value-added (S)-dairy lactone was undertaken from these epoxides and provided the target in 37% overall yield from LGO.

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Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of CMI-977, a Potent 5-Lipoxygenase Inhibitor, published in 1999-02-28, which mentions a compound: 32780-06-6, Name is (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, Molecular C5H8O3, Related Products of 32780-06-6.

5-Lipoxygenase inhibitor (-)-CMI-977 I is prepared as the (2S,5S) enantiomer in nine steps from (S)-glutamic acid, 4-fluorophenol, 3-butynol, and N,O-bis(phenoxycarbonyl)hydroxylamine, and in seven steps from (S)-(+)-hydroxymethyl-γ-butyrolactone.

Although many compounds look similar to this compound(32780-06-6)Related Products of 32780-06-6, numerous studies have shown that this compound(SMILES:O=C1O[C@H](CO)CC1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI

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: 32780-06-6, is researched, Molecular C5H8O3, about Calculations of Cotton effects in the vacuum UV region for chiral γ-lactones: correlation with the absolute stereochemistry, the main research direction is Cotton effect lactone absolute configuration; configuration absolute lactone Cotton effect; CD lactone; ORD lactone.Application In Synthesis of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one.

A graphic method of Drude equations was applied to calculate the Cotton effects below 180 nm region for various types of α- and/or γ-substituted γ-lactones, e.g., I (R1 = H, NH2, NH3Cl; R2 = H, OH; R3 = H, Me) and II (R = H, Br, etc.). The Cotton effects at ∼170 nm were found to reflect the stereochem. at C-2 (neg. for β and pos. for α) and C-4 (pos. for β and neg. for α) as well as the ring conformation (pos. for E3 and neg. for 3E). The rotational contributions at 589 nm were suggested to be the origin of Hudson’s lactone rule.

Although many compounds look similar to this compound(32780-06-6)Application In Synthesis of (S)-5-(Hydroxymethyl)dihydrofuran-2(3H)-one, numerous studies have shown that this compound(SMILES:O=C1O[C@H](CO)CC1), has unique advantages. If you want to know more about similar compounds, you can read my other articles.

Reference:
Metal catalyst and ligand design,
Ligand Template Strategies for Catalyst Encapsulation – NCBI