Category: 57044-25-4

Brun, Elodie published the artcileTotal Synthesis of (+)-Cryptocaryol A Using a Prins Cyclization/Reductive Cleavage Sequence, Synthetic Route of 57044-25-4, the publication is Journal of Organic Chemistry (2015), 80(17), 8668-8676, database is CAplus and MEDLINE.

The total synthesis of (+)-cryptocaryol A (I) was achieved in 20 steps from (R)-glycidol. The key steps were a Prins cyclization/reductive cleavage sequence to construct the C5-C11 polyol fragment, a diastereoselective aldol reaction to control the stereogenic center at C13, and a stereocontrolled reduction to introduce the stereogenic center at C15.

Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Synthetic Route of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Brun, Elodie published the artcileDiastereo- and enantioselective synthesis of 1,3,5,7-tetraol structural units using a Prins cyclisation-reductive cleavage sequence, Synthetic Route of 57044-25-4, the publication is Chemical Communications (Cambridge, United Kingdom) (2014), 50(51), 6718-6721, database is CAplus and MEDLINE.

Stereocontrolled and efficient access to all the diastereomers of 1,3,5,7-tetraol structural units I was developed using a Prins cyclization-reductive cleavage sequence applied to tetrahydropyran aldehydes II. Furthermore, these tetraols can be selectively functionalized.

Chemical Communications (Cambridge, United Kingdom) published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Synthetic Route of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Carneiro, Vania M. T. published the artcileCoibacins A and B: Total Synthesis and Stereochemical Revision, Quality Control of 57044-25-4, the publication is Journal of Organic Chemistry (2014), 79(2), 630-642, database is CAplus and MEDLINE.

The interface between synthetic organic chem. and natural products was explored in order to unravel the structure of coibacin A, a metabolite isolated from the marine cyanobacterium cf. Oscillatoria sp. that exhibits selective antileishmanial activity and potent anti-inflammatory properties. Our synthetic plan focused on a convergent strategy that allows rapid access to the desired target by coupling of three key fragments involving E-selective Wittig and modified Julia olefinations. CD measurements and comparative HPLC analyses of the natural product and four synthetic stereoisomers led to determination of its absolute configuration, thus correcting the original assignment at C-5 and unambiguously establishing those at C-16 and C-18. Therefore, the correct structure is I. Addnl., we synthesized the corrected structure for coibacin B, II, on the basis of the assignment of configuration for coibacin A.

Journal of Organic Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Quality Control of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Araujo, Yara Jaqueline Kerber published the artcileSynthesis and enzymatic resolution of racemic 2,3-epoxy propyl esters obtained from glycerol, Application In Synthesis of 57044-25-4, the publication is Tetrahedron Letters (2015), 56(13), 1696-1698, database is CAplus.

A method is described for the synthesis of (±)-2,3-epoxy Pr esters from glycerol, involving reaction of epichlorohydrin with sodium or potassium salts of carboxylic acids in the presence of TBAB as catalyst, with moderate to excellent yields. Kinetic resolution of glycidyl butyrate by lipase of Thermomyces lanuginosa has been achieved with remarkable enantiomeric excess (ee >99%) using 1,4-dioxane as a co-solvent in pure buffer solution (30 and 50 °C, pH = 7.0).

Tetrahedron Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Sato, Manabu published the artcileTotal Synthesis of (-)-Histrionicotoxin through a Stereoselective Radical Translocation-Cyclization Reaction, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Angewandte Chemie, International Edition (2017), 56(4), 1087-1091, database is CAplus and MEDLINE.

Stereoselective total syntheses of (-)-histrionicotoxin and (-)-histrionicotoxin 235A are described. The 1-azaspiro[5.5]undecane skeleton was constructed diastereoselectively by a radical translocation-cyclization reaction involving a chiral cyclic acetal; the use of tris(trimethylsilyl)silane was crucial for the high diastereoselectivity. The cyclization product was converted into (-)-histrionicotoxin 235A through a one-pot partial-reduction-allylation reaction of a derivative containing an unprotected lactam. Finally, two terminal alkenes were transformed into enynes with the 1,3-amino alc. protected as an oxathiazolidine oxide to complete the total synthesis of (-)-histrionicotoxin.

Angewandte Chemie, International Edition published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Li, Xiaoyong published the artcileStereoselective total synthesis and stereochemistry confirmation of photo-mycolactones, Product Details of C3H6O2, the publication is Tetrahedron Letters (2015), 56(23), 3220-3224, database is CAplus.

With use of the LiTMP-induced Hodgson cyclopropanation of an epoxide-olefin to a bicyclo[3.1.0]hexanol as the key step, a stereoselective total synthesis of photo-mycolactones B1, A1, B2, and A2 was achieved. Each of the four diastereomeric epoxide-olefins, selectively prepared from (R)- and (S)-glycidols, yielded the corresponding unique bicyclo[3.1.0]hexanol. Four bicyclo[3.1.0]hexanols I [R = α-OH, R¹ = α-CH₂OCH₂C₆H₄OMe-4, α-CH₂OCH₂O(CH₂)₂OMe, R² = β-Me, R³ = α-H, R⁴ = β-H; R = β-OH, R¹ = β-CH₂OCH₂C₆H₄OMe-4, α-CH₂OCH₂O(CH₂)₂OMe, R² = α-Me, R³ = β-H, R⁴ = α-H; R = α-OH, R¹ = β-CH₂OCH₂C₆H₄OMe-4, β-CH₂OCH₂O(CH₂)₂OMe, R² = α-Me, R³ = α-H, R⁴ = β-H; R = β-OH, R¹ = α-CH₂OCH₂C₆H₄OMe-4, α-CH₂OCH₂O(CH₂)₂OMe, R² = β-Me, R³ = β-H, R⁴ = α-H] were converted into four primary alcs. II (R = Me, R¹ = α-CH₂OH, R² = β-Me, R³ = α-H, R⁴ = β-H; R = Me, R¹ = β-CH₂OH, R² = α-Me, R³ = β-H, R⁴ = α-H; R = Me, R¹ = β-CH₂OH, R² = α-me, R³ = α-H, R⁴ = β-H; R = Me, R¹ = α-CH₂Oh, R² = β-Me, R³ = β-H, R⁴ = α-H), the intermediates used in the previous work on photo-mycolactones. This synthesis confirmed the stereochem. previously proposed for photo-mycolactones.

Tetrahedron Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Product Details of C3H6O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Norris, Paul C. published the artcileResolvin D3 multi-level proresolving actions are host protective during infection, Product Details of C3H6O2, the publication is Prostaglandins, Leukotrienes and Essential Fatty Acids (2018), 81-89, database is CAplus and MEDLINE.

Resolution of infection and inflammation is governed by innate immune cells. The resolvin family of n-3 mediators produced by resolving exudates stimulates clearance of neutrophils and attenuates pro-inflammatory signals. Using metabololipidomics, endogenous resolvin D3 (RvD3) was identified in self-resolving exudates during active E. coli infection. Through a new, independent synthetic route for RvD3, we matched endogenous and synthetic RvD3 and determined that RvD3 (ng doses) potently reduced the resolution interval (R_i) by ∼4.5 h during E. coli peritonitis after administration at peak inflammation (T_max=12 h) and increased leukocyte phagocytosis of E. coli and neutrophils as well as reduced proinflammatory cytokines, chemokines, MMP-2 and MMP-9. At pM-nM concentrations, RvD3 also enhanced human macrophage efferocytosis and bacterial phagocytosis, increased neutrophil bacterial phagocytosis and intracellular ROS generation, and reduced human platelet-PMN aggregation. These results provide addnl. evidence for potent RvD3 immunoresolvent actions in host defense, host protection and antimicrobial defense.

Prostaglandins, Leukotrienes and Essential Fatty Acids published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Product Details of C3H6O2.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Kajanus, Johan published the artcilePotassium channel blocking 1,2-bis(aryl)ethane-1,2-diamines active as antiarrhythmic agents, Name: (R)-Oxiran-2-ylmethanol, the publication is Bioorganic & Medicinal Chemistry Letters (2019), 29(10), 1241-1245, database is CAplus and MEDLINE.

Herein, synthesis and optimization of a novel series of 1,2-diarylethane-1,2-diamines with selectivity for Kv1.5 over other potassium ion channels is presented. The effective refractory period in the right atrium (RAERP) in a rabbit PD model was investigated for a selection of potent and selective compounds with balanced DMPK properties. The most advanced compound I showed nanomolar potency in blocking Kv1.5 in human atrial myocytes and based on the PD data, the estimated dose to man is 700 mg/day. As previously reported, compound I efficiently converted AF to sinus rhythm in a dog disease model.

Bioorganic & Medicinal Chemistry Letters published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Name: (R)-Oxiran-2-ylmethanol.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts

Bolli, Martin H. published the artcileNovel S1P₁ Receptor Agonists – Part 3: From Thiophenes to Pyridines, Application In Synthesis of 57044-25-4, the publication is Journal of Medicinal Chemistry (2014), 57(1), 110-130, database is CAplus and MEDLINE.

In preceding communications the authors summarized the authors’ medicinal chem. efforts leading to the identification of thiophene derivatives acting as potent, selective, and orally active S1P₁ agonists. As a continuation of these efforts, the authors replaced the thiophene by a 2-, 3-, or 4-pyridine and obtained less lipophilic, potent, and selective S1P₁ agonists (e.g., efficiently reducing blood lymphocyte count in the rat). Structural features influencing the compounds’ receptor affinity profile and pharmacokinetics are discussed. In addition, the ability to penetrate brain tissue has been studied for several compounds As a typical example for these pyridine based S1P₁ agonists, N-((S)-3-{4-[5-(2-Diethylamino-6-methylpyridin4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide showed EC₅₀ values of 0.6 and 352 nM for the S1P₁ and S1P₃ receptor, resp., displayed favorable PK properties, and penetrated well into brain tissue. In the rat, N-((S)-3-{4-[5-(2-Diethylamino-6-methylpyridin4-yl)[1,2,4]oxadiazol-3-yl]-2-ethyl-6-methylphenoxy}-2-hydroxypropyl)-2-hydroxyacetamide maximally reduced the blood lymphocyte count for at least 24 h after oral dosing of 3 mg/kg.

Journal of Medicinal Chemistry published new progress about 57044-25-4. 57044-25-4 belongs to alcohols-buliding-blocks, auxiliary class Epoxides,Chiral,Aliphatic hydrocarbon chain,Alcohol, name is (R)-Oxiran-2-ylmethanol, and the molecular formula is C3H6O2, Application In Synthesis of 57044-25-4.

Referemce:
https://en.wikipedia.org/wiki/Alcohol,
Alcohols – Chemistry LibreTexts