Category: 57044-25-4

Scuotto, M. published the artcileOutstanding effects on antithrombin activity of modified TBA diastereomers containing an optically pure acyclic nucleotide analogue, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Organic & Biomolecular Chemistry (2014), 12(28), 5235-5242, database is CAplus and MEDLINE.

Herein, we report optically pure modified acyclic nucleosides as ideal probes for thrombin binding aptamer (TBA) modification. These new monomers offer unique advantages in exploring the role played in thrombin inhibition by a single residue modification at key positions of the TBA structure.

Organic & Biomolecular 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 C16H20N2, Recommanded Product: (R)-Oxiran-2-ylmethanol.

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

Straker, R. N. published the artcileComputational ligand design in enantio- and diastereoselective ynamide [5+2] cycloisomerization, Recommanded Product: (R)-Oxiran-2-ylmethanol, the publication is Nature Communications (2016), 10109, database is CAplus and MEDLINE.

Many diastereoselective (substrate stereocontrol), and enantioselective (catalyst stereocontrol) cycloisomerizations was developed. However, asym. cycloisomerizations where a chiral catalyst specifies the stereochem. outcome of the cyclization of a single enantiomer substrate-regardless of its inherent preference-were unknown. A combined theor. and exptl. approach enables the design of a highly reactive rhodium catalyst for the stereoselective cycloisomerization of ynamide-vinylcyclopropanes to [5.3.0]-azabicycles was showed. Highly diastereoselective cycloisomerizations using an achiral catalyst, and then explored phosphoramidite-complexed rhodium catalysts in the enantioselective variant, where theor. investigations uncovered an unexpected reaction pathway in which the electronic structure of the phosphoramidite dramatically influences reaction rate and enantioselectivity was established. A marked enhancement of both was observed using the optimal theory-designed ligand, which enabled double stereodifferentiating cycloisomerizations in both matched and mismatched catalyst-substrate settings.

Nature Communications 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 C20H22ClN3O3, Recommanded Product: (R)-Oxiran-2-ylmethanol.

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

Ricciardi, Maria published the artcileGlycidol, a Valuable Substrate for the Synthesis of Monoalkyl Glyceryl Ethers: A Simplified Life Cycle Approach, Related Products of alcohols-buliding-blocks, the publication is ChemSusChem (2017), 10(10), 2291-2300, database is CAplus and MEDLINE.

The disposal of any waste by recovering it within the production plant represents the ultimate goal of every biorefinery. In this scenario, the selective preparation of monoalkyl glyceryl ethers (MAGEs) starting from glycidol, obtained as byproduct in the epichlorohydrin production plant, represents a very promising strategy. Here, we report the synthesis of MAGEs through the reaction of glycidol with alcs. catalyzed by a green homogeneous Lewis acids catalyst, such as Bi^III triflate, under very mild reaction conditions. To evaluate the green potential of the proposed alternative, a simplified life cycle assessment (LCA) approach was followed by comparing the environmental performance of the proposed innovative route to prepare MAGEs with that of the most investigated pathway from glycerol. A considerable reduction of all impact categories considered was observed in our exptl. conditions, suggesting that the glycidol-to-MAGEs route can be a valuable integration to the glycerol-to-MAGEs chain. Thanks to the use of primary data within the LCA model, the results achieved are a very good approximation of the real case.

ChemSusChem 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, Related Products of alcohols-buliding-blocks.

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

Morita, Masao published the artcileTotal Syntheses of Perenniporides, Product Details of C3H6O2, the publication is Organic Letters (2015), 17(22), 5634-5637, database is CAplus and MEDLINE.

The total syntheses of perenniporide A (I) and related compounds have been achieved. Starting from 1,3,5-trifluorobenzene, difluorodienone II was obtained by oxidative dearomatization, which served as a platform for the high-pressure cycloaddition and for the introduction of the C3-methoxy group. The synthesis allowed access to the natural congeners III and IV, enabling assignment of the absolute structures of these natural products.

Organic 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

Twum, Elvis A. published the artcileInitial development of a cytotoxic amino-seco-CBI warhead for delivery by prodrug systems, COA of Formula: C3H6O2, the publication is Bioorganic & Medicinal Chemistry (2015), 23(13), 3481-3489, database is CAplus and MEDLINE.

Cyclopropabenzaindoles (CBIs) are exquisitely potent cytotoxins which bind and alkylate in the minor groove of DNA. They are not selective for cancer cells, so prodrugs are required. CBIs can be formed at physiol. pH by Winstein cyclisation of 1-chloromethyl-3-substituted-5-hydroxy-2,3-dihydrobenzo[e]indoles (5-OH-seco-CBIs). Corresponding 5-NH₂-seco-CBIs should also undergo Winstein cyclisation similarly. A key triply orthogonally protected intermediate on the route to 5-NH₂-seco-CBIs has been synthesized, via selective monotrifluoroacetylation of naphthalene-1,3-diamine, Boc protection, electrophilic iodination, selective allylation at the trifluoroacetamide and 5-exo radical ring-closure with TEMPO. This intermediate has potential for introduction of peptide prodrug masking units (deactivating the Winstein cyclisation and cytotoxicity), addition of diverse indole-amide side-chains (enhancing non-covalent binding prior to alkylation) and use of different leaving groups (replacing the usual chlorine, allowing tuning of the rate of Winstein cyclisation). This key intermediate was elaborated into a simple model 5-NH₂-seco-CBI with a dimethylaminoethoxyindole side-chain. Conversion to a bio-reactive entity and the bioactivity of this system were confirmed through DNA-melting studies (ΔT_m = 13 °C) and cytotoxicity against LNCaP human prostate cancer cells (IC₅₀ = 18 nM).

Bioorganic & 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 C6H20Cl2N4, COA of Formula: C3H6O2.

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

Moriyama, Mizuki published the artcileDivergent asymmetric total synthesis of all four pestalotin diastereomers from (R)-glycidol, Related Products of alcohols-buliding-blocks, the publication is Molecules (2020), 25(2), 394, database is CAplus and MEDLINE.

All four chiral pestalotin diastereomers were synthesized in a straightforward and divergent manner from common (R)-glycidol. Catalytic asym. Mukaiyama aldol reactions of readily-available bis(TMSO)diene (Chan’s diene) with (S)-2-benzyloxyhexanal derived from (R)-glycidol produced a syn-aldol adduct with high diastereoselectivity and enantioselectivity using a Ti(iOPr)₄/(S)-BINOL/LiCl catalyst. Diastereoselective Mukaiyama aldol reactions mediated by catalytic achiral Lewis acids directly produced not only a (1’S,6S)-pyrone precursor via the syn-aldol adduct using TiCl₄, but also (1’S,6R)-pyrone precursor via the antialdol adduct using ZrCl₄, in a stereocomplementary manner. A Hetero-Diels-Alder reaction of similarly available mono(TMSO)diene (Brassard’s diene) with (S)-2-benzyloxyhexanal produced the (1’S,6S)-pyrone precursor promoted by Eu(fod)₃ and the (1’S,6R)-pyrone precursor Et₂AlCl. Debenzylation of the (1’S,6S)-precursor and the (1’S,6R)-precursor furnished natural (-)-pestalotin (99% ee, 7 steps) and unnatural (+)-epipestalotin (99% ee, 7 steps), resp. Mitsunobu inversions of the obtained (-)-pestalotin and (+)-epipestalotin successfully produced the unnatural (+)-pestalotin (99% ee, 9 steps) and (-)-epipestalotin (99% ee, 9 steps), resp., in a divergent manner. All four of the obtained chiral pestalotin diastereomers possessed high chem. and optical purities (optical rotations, 1H-NMR, 13C-NMR, and HPLC measurements).

Molecules 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, Related Products of alcohols-buliding-blocks.

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

Nakamura, Masaharu published the artcileDevelopment of silicon-containing bis-phenol derivatives as androgen receptor antagonists: Selectivity switching by C/Si exchange, SDS of cas: 57044-25-4, the publication is Bioorganic & Medicinal Chemistry (2013), 21(7), 1643-1651, database is CAplus and MEDLINE.

The authors previously reported that bis-phenol derivatives, including LG190178, possess not only vitamin D receptor (VDR) agonistic activity, but also androgen receptor (AR) antagonistic activity. Here, the authors describe the design, synthesis and evaluation of silicon-containing bis-phenol derivatives, with the objective of obtaining increased selectivity toward VDR or AR. The authors found that replacement of the quaternary carbon in the bis-phenol skeleton with silicon increased AR-antagonistic activity and reduced VDR-agonistic activity, i.e., the AR selectivity of the silicon-containing compounds was higher than that of corresponding carbon compounds To the authors’ knowledge, this is the first report of nuclear receptor (NR) selectivity switching by sila-substitution (C/Si exchange). Among the compounds synthesized, AR-selective ligand (I) exhibited more potent anti-androgenic activity (IC₅₀ = 0.072 μM) than hydroxyflutamide, a well-known androgen antagonist (IC₅₀ = 1.4 μM), in SC-3 cell proliferation assay. These results suggest that sila-substitution is a useful approach for structural development of selective AR ligands.

Bioorganic & 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, SDS of cas: 57044-25-4.

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

Sanceau, Jean-Yves published the artcileTotal Synthesis of the Antidiabetic (Type 2) Lipid Mediator Protectin DX/PDX, Name: (R)-Oxiran-2-ylmethanol, the publication is Journal of Organic Chemistry (2019), 84(2), 495-505, database is CAplus and MEDLINE.

The first total synthesis of a lipid mediator derived from natural ω-3-fatty acid docosahexaenoic acid (DHA), 10S,17S-diHDHA (also referred to as protectin DX/PDX), was achieved in a convergent route (29 steps). The two chiral hydroxyl groups at C-10 and C-17 were derived from readily available (S)-1,2,4-butanetriol and (R)-glycidol, resp. The two stereodefined E-double bonds were generated by a Takai olefination, and the skipped diene side chain was introduced with a stereocontrolled Wittig olefination. Importantly, the sensitive conjugated E,Z,E-triene intermediate was generated by a Boland reduction of the central triple bond of a E,E-dienyne. Overall, this synthetic strategy should allow the preparation of a larger quantity of PDX, which is inaccessible via previously reported biosynthetic approaches.

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, Name: (R)-Oxiran-2-ylmethanol.

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

Shiau, Timothy P. published the artcileSulfonyl-polyol N,N-dichloroamines with rapid, broad-spectrum antimicrobial activity, Name: (R)-Oxiran-2-ylmethanol, the publication is Bioorganic & Medicinal Chemistry Letters (2013), 23(20), 5650-5653, database is CAplus and MEDLINE.

The discovery and development of antimicrobial agents that do not give rise to resistance remains an ongoing challenge. Our efforts in this regard continue to reveal new potential therapeutic agents with differing physicochem. properties while retaining the effective N,N-dichloroamine pharmacophore as the key antimicrobial warhead. In this Letter, disclosed are agents containing polyol units as a water solubilizing group. These sulfonyl-polyol agents show broad spectrum bactericidal and virucidal activity. These compounds show 1h MBC’s of 16-512 μg/mL against Escherichia coli and 4-256 μg/mL against Staphylococcus aureus at neutral pH, and 1-h IC₅₀‘s of 4.5-32 μM against Adenovirus 5 and 0.7-3.0 μM against Herpes simplex virus 1. The lead compounds were tested in a tissue culture irritancy assay and showed only minimal irritation at the highest concentrations tested.

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 C14H18BNO2, Name: (R)-Oxiran-2-ylmethanol.

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

He, Yu-Tao published the artcileSynthesis of Various Bridged Ring Systems via Rhodium-Catalyzed Bridged (3+2) Cycloadditions, Name: (R)-Oxiran-2-ylmethanol, the publication is Organic Letters (2022), 24(1), 186-190, database is CAplus and MEDLINE.

Here, the authors describe the rhodium-catalyzed bridged [3+2]-cycloaddition cascade reactions of N-sulfonyl-1,2,3-triazoles, which allowed the efficient diastereoselective construction of various functionalized and synthetically challenging bridged ring systems. This simple, direct transformation had a broad substrate scope and excellent functional group tolerance. The highly strained polycyclic bicyclo[2.2.2]octa[b]indole core of fruticosine was synthesized efficiently using this methodol.

Organic 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