Category: 20880-92-6

Heuckendorff, Mads published the artcileDIDMH in combination with triflic acid – A new promoter system for thioglycoside glycosyl donors, Product Details of C12H20O6, the publication is Carbohydrate Research (2018), 86-91, database is CAplus and MEDLINE.

We have explored the possibility of using 1,3-diiodo-5,5-dimethylhydantoin (DIDMH) as an alternative to N-iodosuccinimide (NIS) for activation of glycosyl donors of the thioglycoside type in various glycosylation reactions. DIDMH was found to match NIS when it comes to the capability to activate thioglycosides and provide glycosylation products in good yields. Notably, with the two equivalent of reactive iodonium ions per mol. of DIDMH less mass needs to be added making this activator a more atom economically alternative to NIS. Furthermore, DIDMH was found to be stable upon storage for weeks and comparably priced to NIS. With this knowledge in hand we therefore encourage the carbohydrate community to consider using DIDMH for activation of thioglycosides in glycosylation reactions.

Carbohydrate Research published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Product Details of C12H20O6.

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

Pestova, S. V. published the artcileSynthesis and membrane protective activity of bis-sulfides derived from monoterpenoids and monosaccharides, Product Details of C12H20O6, the publication is Russian Journal of Bioorganic Chemistry (2017), 43(3), 302-310, database is CAplus.

Hydroxyl- and chloroethyl derivatives of neomenthane- and isobornanethiol in yields of to 80% were synthesized. They served as the basis for the preparation of new bis-sulfides with diacetone-protected galacto- and fructopyranose fragments in yields up to 98%. The bis-sulfides synthesized were screened for membrane protective and antioxidant properties in a model cell system (in vitro) based on their ability to inhibit the H₂O₂-induced hemolysis of erythrocytes and retard the oxy-Hb oxidation

Russian Journal of Bioorganic Chemistry published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Product Details of C12H20O6.

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

Pestova, S. V. published the artcileSynthesis and membranoprotective properties of new disulfides with monoterpene and carbohydrate fragments, Computed Properties of 20880-92-6, the publication is Russian Chemical Bulletin (2015), 64(3), 723-731, database is CAplus.

A cooxidn. of carbohydrate and terpene thiols gives mixtures of disulfides containing 51-90% of the unsym. product. Membranoprotective and antioxidant properties of obtained unsym. and sym. disulfides were evaluated based on their ability to inhibit the H₂O₂-induced hemolysis of erythrocytes, as well as the accumulation of secondary products of the peroxy oxidation of lipids and the oxidation of Hb.

Russian Chemical Bulletin published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Computed Properties of 20880-92-6.

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

Watanabe, Bunta published the artcileSynthesis and inhibitory activity of substrate-analog fructosyl peptide oxidase inhibitors, SDS of cas: 20880-92-6, the publication is Bioorganic & Medicinal Chemistry Letters (2015), 25(18), 3910-3913, database is CAplus and MEDLINE.

Fructosyl peptide oxidases (FPOXs) play a crucial role in the diagnosis of diabetes. Their main function is to cleave fructosyl amino acids or fructosyl peptides into glucosone and the corresponding amino acids/dipeptides. In this study, the substrate-analog FPOX inhibitors were successfully designed and synthesized. These glycosyl-amino acid inhibitors mimic N^α-fructosyl-L-valine (Fru-Val), [N^α-fructosyl-L-valyl]-L-histidine (Fru-ValHis), and N^ε-fructosyl-L-lysine (εFru-Lys), resp. The secondary nitrogen atom in the natural substrates, linking fructose and amino acid or dipeptide moieties, was substituted in glycosyl-amino acids with a sulfur atom to avoid enzymic cleavage. Kinetic studies revealed that prepared glycosyl-amino acids act as competitive inhibitors against an FPOX obtained from Coniochaeta sp., and K_i values of 11.1, 66.8, and 782 μM were obtained.

Bioorganic & Medicinal Chemistry Letters published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H15BF2O2, SDS of cas: 20880-92-6.

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

Schoch, Silvia published the artcileTethering Carbohydrates to the Vinyliminium Ligand of Antiproliferative Organometallic Diiron Complexes, Computed Properties of 20880-92-6, the publication is Organometallics (2022), 41(5), 514-526, database is CAplus and MEDLINE.

Four propargyl O-glycosides derivatized with mannose, glucose, and fructose moieties were synthesized and then incorporated within a diiron structure as part of a vinyliminium ligand. Hence, six glycoconjugated diiron complexes, [2–5]CF₃SO₃ (see Scheme 1) and the nonglycosylated analogs [6a–b]CF₃SO₃, were obtained in high yields and unambiguously characterized by elemental anal., mass spectrometry, and IR and multinuclear NMR spectroscopies. All compounds exhibited a significant stability in DMSO-d₆/D₂O solution, with 63-89% of the complexes unaltered after 72 h at 37° and also in the cell culture medium. The cytotoxicity of [2–6]CF₃SO₃, as well as that of previously reported 7 and 8, was assessed on CT26 (mouse colon carcinoma), U87 (human glioblastoma), MCF-7 (human breast adenocarcinoma), and RPE-1 (human normal retina pigmented epithelium) cell lines. In general, the IC₅₀ values correlate with the hydrophobicity of the compounds (measured as octanol-H₂O partition coefficients) and do not show an appreciable level of selectivity against cancer cells with respect to the nontumor ones.

Organometallics published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Computed Properties of 20880-92-6.

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

Yoshida, Tatsuki published the artcileTransition-Metal-Free O-Arylation of Alcohols and Phenols with S-Arylphenothiaziniums, Recommanded Product: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, the publication is Journal of Organic Chemistry (2022), 87(11), 7565-7573, database is CAplus and MEDLINE.

Herein, authors report the transition-metal-free O-arylation of alcs. and phenols with S-arylphenothiaziniums, which can be easily synthesized from boronic acids. Aryl substituents derived from arylboronic acids were selectively introduced into the hydroxy groups in alcs. and phenols, and a variety of aryl ethers were synthesized. This selectivity is supported by theor. calculations

Journal of Organic Chemistry published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C8H5F3O3, Recommanded Product: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol.

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

Andersen, Sofie Meng published the artcile3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry, Computed Properties of 20880-92-6, the publication is Organic Letters (2015), 17(4), 944-947, database is CAplus and MEDLINE.

Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatog. purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

Organic Letters published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Computed Properties of 20880-92-6.

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

Zhang, Zhenzhen published the artcileSilver-Mediated N-Trifluoromethylation of Amides and Peptides, Recommanded Product: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, the publication is Chinese Journal of Chemistry (2020), 38(9), 924-928, database is CAplus.

The direct N-trifluoromethylation of N-H amides was reported. Promoted by AgOTf and 2-fluoropyridine, the reaction of a variety of amides with Selectfluor, TMSCF₃ and CsF proceeded smoothly at room temperature leading to the corresponding N-trifluoromethylated products in satisfactory yields. The protocol was also applicable to amino acid derivatives, resulting in efficient and chemoselective N-trifluoromethylation of di- and tri-peptides with retention of configuration. A mechanism involving reductive elimination of Ag(III) intermediates to form N-CF₃ bonds was proposed.

Chinese Journal of Chemistry published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C28H41N7O4, Recommanded Product: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol.

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

Chen, Yi-Xuan published the artcilePhotochemical Organocatalytic Aerobic Cleavage of C=C Bonds Enabled by Charge-Transfer Complex Formation, Name: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, the publication is Organic Letters (2022), 24(22), 3920-3925, database is CAplus and MEDLINE.

A novel visible-light-driven organocatalytic protocol to access aerobic oxidative cleavage of olefins, e.g., 4-benzylidene-2,6-di-tert-butylcyclohexa-2,5-dien-1-one promoted by sodium benzene sulfinate, is described. An array of alkenes smoothly delivered the corresponding aldehydes RC(O)R¹ (R = naphth-2-yl, 2-chlorophenyl, 3,4-dimethoxyphenyl, etc.; R¹ = H) and ketones, e.g., 2, 6-di-tert-butylcyclohexa-2, 5-diene-1,4-dione under transition-metal-free conditions. Notably, α-halo-substituted styrenes, e.g., (1-bromovinyl)benzene proceeded with photoinduced oxidation to finally afford α-halo-acetophenones, e.g., 2-bromo-1-phenylethan-1-one with halogen migration. Crucial to this oxidation was the formation of charge-transfer complexes between sodium benzene sulfinate with mol. O₂ to ultimately deliver the carbonyl products.

Organic Letters published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Name: ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol.

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

Fejes, Zsolt published the artcileSynthesis of ether-linked [60]fullerene glycoconjugates by nucleophilic cyclopropanation, Safety of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, the publication is Chemical Papers (2015), 69(6), 896-900, database is CAplus.

Et acetoacetate-sugar derivatives were prepared by standard alkylation of primary or secondary hydroxyls of diacetonide-protected sugars with Et 4-chloroacetoacetate. The obtained D-fructose, D-galactose, D-glucose and F-allose derivatives were conjugated to C₆₀ using the Bingel reaction to afford hydrolytically stable, ether-linked fullerene-carbohydrates. Conjugation of an ester-protected mannose derivative to the C₆₀ scaffold was carried out by the combination of the acetoacetate chem. with the azide-alkyne click reaction.

Chemical Papers published new progress about 20880-92-6. 20880-92-6 belongs to alcohols-buliding-blocks, auxiliary class Other Aliphatic Heterocyclic,Chiral,Alcohol, name is ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol, and the molecular formula is C12H20O6, Safety of ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol.

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