Day: November 21, 2022

Zavgorodnii, S. published the artcile1-Alkylthioalkylation of nucleoside hydroxyl functions and its synthetic applications: a new versatile method in nucleoside chemistry, Synthetic Route of 87865-78-9, the publication is Tetrahedron Letters (1991), 32(51), 7593-6, database is CAplus.

Treatment of appropriately protected nucleosides I (B = Thy, BzCyt, BzAde, IbGua; R = H) with a mixture of acetic acid, acetic anhydride and dialkyl sulfoxide was shown to give O-(1-alkylthioalkylated) nucleosides I (R = CH₂SMe) that were oxidized to the corresponding sulfoxides and sulfones I [R = CH₂S(O)_nMe, n = 1, 2], or converted via O-halomethyl derivatives I (R = CH₂Br, CH₂Cl) to various O-substituted nucleosides, e.g., II, [B¹ = Thy, Cyt, Ade, Gua; R¹ = CH₂F, CH₂N₃, CH₂CN, CH₂OMe, CH₂P(O)(OH)₂].

Tetrahedron Letters published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C12H9NO, Synthetic Route of 87865-78-9.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Yu, Tzu-Yu published the artcileSafe, Scalable, Inexpensive, and Mild Nickel-Catalyzed Migita-Like C-S Cross-Couplings in Recyclable Water, Application of 2-Methyl-3-tetrahydrofuranthiol, the publication is Angewandte Chemie, International Edition (2021), 60(7), 3708-3713, database is CAplus and MEDLINE.

A new approach to C-S couplings is reported that relies on nickel catalysis under mild conditions, enabled by micellar catalysis in recyclable water as the reaction medium. The protocol tolerates a wide range of heteroaromatic halides and thiols, including alkyl and heteroaryl thiols, leading to a variety of thioethers in good isolated yields. The method is scalable, results in low residual metal in the products, and is applicable to syntheses of targets in the pharmaceutical area. The procedure also features an associated low E Factor, suggesting a far more attractive entry than is otherwise currently available, especially those based on unsustainable loadings of Pd catalysts.

Angewandte Chemie, International Edition published new progress about 57124-87-5. 57124-87-5 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Thiol, name is 2-Methyl-3-tetrahydrofuranthiol, and the molecular formula is C8H8O3, Application of 2-Methyl-3-tetrahydrofuranthiol.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Chen, Jinxiang published the artcilePyrolysis volatiles and environmental impacts of printing paper in air, COA of Formula: C4H6O3, the publication is Cellulose (Dordrecht, Netherlands) (2014), 21(4), 2871-2878, database is CAplus.

Pyrolysis volatiles and the environmental impact of printing paper in an air atm. were investigated using pyrolysis-gas chromatog./mass spectrometry and SEM. CO₂ and light-pollution products were found to be the major products from pyrolysis volatiles; furthermore, because oxygen participates in the chem. reaction, many of the pyrolysis volatiles emitted during the paper printing process were different from those formed under an N₂ atmosphere. Although a small number of the volatiles were moderately toxic products, the concentrations of these volatiles were low. Heat-induced inkless eco-printing (HIEP) was found to take less time than the pyrolysis experiment in this paper and thus resulted in fewer pyrolysis volatiles. Thus, fewer pyrolysis volatiles will be emitted within the practical temperature range; in particular, no carcinogens were emitted in the pyrolysis temperature range of 250-700 °C. Therefore, HIEP was found to be an ecol. and environmentally preferable technol.

Cellulose (Dordrecht, Netherlands) published new progress about 19444-84-9. 19444-84-9 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Ester,Alcohol, name is 3-Hydroxydihydrofuran-2(3H)-one, and the molecular formula is C4H6O3, COA of Formula: C4H6O3.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Gibbons, Garrett S. published the artcileRegulation of Wnt Signaling Target Gene Expression by the Histone Methyltransferase DOT1L, Formula: C28H41N7O4, the publication is ACS Chemical Biology (2015), 10(1), 109-114, database is CAplus and MEDLINE.

The histone methyltransferase DOT1L, solely responsible for histone H3 lysine 79 (H3K79) methylation, is associated with gene activation. Human leukemias carrying MLL gene rearrangements aberrantly recruit DOT1L to leukemogenic genes leading to increased H3K79 methylation and their transcriptional activation. Recent studies suggest that Wnt-targeted genes also depend on H3K79 methylation. Employing a chem. biol. approach, the requirement for H3K79 methylation was investigated in Wnt pathway-inducible HEK293 cells and human colon adenocarcinoma-derived cell lines by inhibiting DOT1L with EPZ004777, a selective and potent S-adenosylmethionine competitive inhibitor. Our findings indicate that H3K79 methylation is not essential for the canonical Wnt signaling pathway, in particular for maintenance or activation of Wnt pathway target gene expression. Furthermore, H3K79 methylation is not elevated in human colon carcinoma samples in comparison with normal colon tissue. Therefore, our findings indicate that inhibition of DOT1L histone methyltransferase activity is likely not a viable therapeutic strategy in colon cancer.

ACS Chemical Biology published new progress about 1338466-77-5. 1338466-77-5 belongs to tetrahydrofurans, auxiliary class Epigenetics,Histone Methyltransferase, name is 1-(3-((((2R,3S,4R,5R)-5-(4-Amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea, and the molecular formula is C28H41N7O4, Formula: C28H41N7O4.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Seow, Yi-Xin published the artcileOdor-specific loss of smell sensitivity with age as revealed by the specific sensitivity test, Synthetic Route of 57124-87-5, the publication is Chemical Senses (2016), 41(6), 487-495, database is CAplus and MEDLINE.

The perception of odor mixtures plays an important role in human food intake, behavior, and emotions. Decline of smell acuity with normal aging could impact food perception and preferences at various ages. However, since the landmark Smell Survey by National Geog., little has been elucidated on differences in the onset and extent of loss in olfactory sensitivity toward single odorants. Here, using the Specific Sensitivity test, we show the onset and extent of loss in both identification and detection thresholds of odorants with age are odorant-specific. Subjects of Chinese descent in Singapore (186 women, 95 men), aged 21-80 years, were assessed for olfactory sensitivity of 10 odorants from various odor groups. Notably, subjects in their 70s required 179 times concentration of rose-like odorant (2-phenylethanol) than subjects in the 20s, while thresholds for onion-like 2-methyloxolane-3-thiol only differed by 3 times between the age groups. In addition, identification rate for 2-phenylethanol was neg. correlated with age throughout adult life whereas mushroom-like oct-1-en-3-ol was equally identified by subjects across all ages. Our results demonstrated the girth of differentiated olfactory loss due to normal ageing, which potentially affect overall perception and preferences of odor mixtures with age.

Chemical Senses published new progress about 57124-87-5. 57124-87-5 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Thiol, name is 2-Methyl-3-tetrahydrofuranthiol, and the molecular formula is CBF6K, Synthetic Route of 57124-87-5.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Daigle, Scott R. published the artcileSelective Killing of Mixed Lineage Leukemia Cells by a Potent Small-Molecule DOT1L Inhibitor, Category: tetrahydrofurans, the publication is Cancer Cell (2011), 20(1), 53-65, database is CAplus and MEDLINE.

Mislocated enzymic activity of DOT1L has been proposed as a driver of leukemogenesis in mixed lineage leukemia (MLL). The characterization of EPZ004777, a potent, selective inhibitor of DOT1L is reported. Treatment of MLL cells with the compound selectively inhibits H3K79 methylation and blocks expression of leukemogenic genes. Exposure of leukemic cells to EPZ004777 results in selective killing of those cells bearing the MLL gene translocation, with little effect on non-MLL-translocated cells. Finally, in vivo administration of EPZ004777 leads to extension of survival in a mouse MLL xenograft model. These results provide compelling support for DOT1L inhibition as a basis for targeted therapeutics against MLL.

Cancer Cell published new progress about 1338466-77-5. 1338466-77-5 belongs to tetrahydrofurans, auxiliary class Epigenetics,Histone Methyltransferase, name is 1-(3-((((2R,3S,4R,5R)-5-(4-Amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)(isopropyl)amino)propyl)-3-(4-(tert-butyl)phenyl)urea, and the molecular formula is C28H41N7O4, Category: tetrahydrofurans.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Ohtsuka, Eiko published the artcileStudies on transfer ribonucleic acids and related compounds. XLIV. A large-scale synthesis of the anticodon heptanucleotide of formyl-methionine transfer ribonucleic acid by using 2′-O-tetrahydrofuranylnucleosides, Recommanded Product: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Chemical & Pharmaceutical Bulletin (1983), 31(6), 1910-16, database is CAplus and MEDLINE.

2′-O-Tetrahydrofuranyl nucleosides were prepared by an improved procedure via 3′,5′-tetraisopropyldisiloxanyl nucleosides. A large-scale synthesis of the anticodon heptanucleotide C-U-C-A-U-A-A of Escherichia coli formylmethionine tRNA was performed by the phosphotriester method involving condensation of oligonucleotides having 2′-O-tetrahydrofuranyl protecting groups.

Chemical & Pharmaceutical Bulletin published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Recommanded Product: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Van de Vyver, Stijn published the artcileSolid Lewis Acids Catalyze the Carbon-Carbon Coupling between Carbohydrates and Formaldehyde, Name: 3-Hydroxydihydrofuran-2(3H)-one, the publication is ACS Catalysis (2015), 5(2), 972-977, database is CAplus.

The development of catalytic C-C bond formation schemes based on renewable substrates is important for defining sustainable paradigms for chem. manufacturing With a few exceptions, aldol condensation reactions between biomass-derived platform chems. have received little attention so far. Here the C-C coupling between 1,3-dihydroxyacetone (DHA) and formaldehyde into α-hydroxy-γ-butyrolactone (HBL) using Sn-Beta is demonstrated. Reactivity studies, coupled with spectroscopic and computational analyses, show that the formation of HBL proceeds by soft enolization of DHA followed by an aldol addition of formaldehyde to the Sn-enolate intermediate, generating erythrulose as an intermediate species. Isotopic labeling is used to reveal the position where formaldehyde is incorporated into HBL, providing further support for our proposed mechanism. Finally, combining the C-C coupling reaction with transfer hydrogenation of formaldehyde has allowed us to expand the substrate scope to include polyols glycerol and ethylene glycol.

ACS Catalysis published new progress about 19444-84-9. 19444-84-9 belongs to tetrahydrofurans, auxiliary class Tetrahydrofuran,Ester,Alcohol, name is 3-Hydroxydihydrofuran-2(3H)-one, and the molecular formula is C21H26Br4S2, Name: 3-Hydroxydihydrofuran-2(3H)-one.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Hayashi, Junsuke published the artcileSyntheses of prodrug-type 2′-O-methyldithiomethyl oligonucleotides modified at natural four nucleoside residues and their conversions into natural 2′-hydroxy oligonucleotides under reducing condition, Name: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Bioorganic & Medicinal Chemistry (2018), 26(22), 5838-5844, database is CAplus and MEDLINE.

We previously reported that reducing-environment-responsive prodrug-type small interfering RNA (siRNA) bearing 2′-O-methyldithiomethyl (2′-O-MDTM) uridine exhibits efficient knockdown activity and nuclease resistance. In this report, we describe the preparation of 2′-O-MDTM oligonucleotides modified not only at uridine but also at adenosine, guanosine and cytidine residues by post-synthetic modification. Precursor oligonucleotides bearing 2′-O-(2,4,6-trimethoxybenzylthiomethyl) (2′-O-TMBTM) adenosine, guanosine, and cytidine were reacted with dimethyl(methylthio)sulfonium tetrafluoroborate to form 2′-O-MDTM oligonucleotides in the same manner as the oligonucleotide bearing 2′-O-TMBTM uridine. Furthermore, the oligonucleotides bearing 2′-O-MDTM adenosine, guanosine, and cytidine were efficiently converted into corresponding natural 2′-hydroxy oligonucleotides under the cytosol-mimetic reducing condition.

Bioorganic & Medicinal Chemistry published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Name: N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem

Markiewicz, Wojciech T. published the artcileStudies on synthesis and structure of O-β-D-ribofuranosyl(1”→2′)ribonucleosides and oligonucleotides, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, the publication is Nucleosides & Nucleotides (1998), 17(1-3), 411-424, database is CAplus.

Minor nucleosides found in several eukaryotic initiator tRNAs₁^Met, O-β-D-ribofuranosyl(1”→2′)adenosine and -guanosine (Ar and Gr), as well as their pyrimidine analogs, were obtained from N-protected 3′,5′-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)ribonucleosides and 1-O-acetyl-2,3,5-tri-O-benzoyl-β-D-ribofuranose in the presence of tin tetrachloride in 1,2-dichloroethane. A crystal structure has been solved for 2′-O-ribosyluridine. The 3′-phosphoramidites of protected 2′-O-ribosylribonucleosides were prepared as the reagents for 2′-O-ribofuranosyloligonucleotides synthesis. O-β-D-Ribofuranosyl(1”→2′)adenylyl(3’→5′)guanosine (ArpG) was obtained and its structure was analyzed by NMR spectroscopy.

Nucleosides & Nucleotides published new progress about 87865-78-9. 87865-78-9 belongs to tetrahydrofurans, auxiliary class Nucleosides and Nucleotides,Nucleoside Analogues, name is N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide, and the molecular formula is C26H45N5O7Si2, Safety of N-(9-((6aR,8R,9R,9aS)-9-Hydroxy-2,2,4,4-tetraisopropyltetrahydro-6H-furo[3,2-f][1,3,5,2,4]trioxadisilocin-8-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)isobutyramide.

Referemce:
https://en.wikipedia.org/wiki/Tetrahydrofuran,
Tetrahydrofuran | (CH2)3CH2O – PubChem