582-52-5Relevant articles and documents
Direct Access to 2,3,4,6-Tetrasubstituted Tetrahydro-2H-pyrans via Tandem SN2′-Prins Cyclization
Scoccia, Jimena,Pérez, Sixto J.,Sinka, Victoria,Cruz, Daniel A.,López-Soria, Juan M.,Fernández, Israel,Martín, Víctor S.,Miranda, Pedro O.,Padrón, Juan I.
, p. 4834 - 4837 (2017)
A new, direct, and diastereoselective synthesis of activated 2,3,4,6-tetrasubstituted tetrahydro-2H-pyrans is described. In this reaction, iron(III) catalyzed an SN2′-Prins cyclization tandem process leading to the creation of three new stereoc
Properties, stability, assay, and preliminary pharmacokinetics of the immunomodulatory 1,2-O-isopropylidene-3-O-3'(N',N'-dimethylamino-n-propyl)-D-glucofuranose hydrochloride
Garrett,Van Peer,Mahrous,Schuermann
, p. 387 - 395 (1982)
1,2-O-Isopropylidene-3-O-3(N',N'-dimethylamino-n-propyl)-D-glucufuranose hydrochloride (I) is a new agent with claimed immunomodulatory action and antiviral activity. Thin-layer chromatographic procedures and identifying tests were developed to separate the drug, its synthetic precursors, and solvolytic products, and were applied to stability studies. It is stable in 0.1N NaOH at 60° where its acid solvolysis product, 3-O-3'-(N',N'-dimethylamino-n-propyl)-D-glucose is readily degraded. The partition coefficient of I (pK'(a)=9.28) between chloroform and plasma was 6.4 ± 0.2 SEM between pH 10.5 and 11.0. Plasma and urine (0.5ml) adjusted to pH 11.0 were extracted with 10 ml of chloroform and the extract evaporated. The reconstituted residue in 50 μl of benzene, with the diiopropylaminoethyl analog of I as an internal standard, was derivatized with 50 μl of heptafluorobutyric anhydride at 60° for 45 min and was evaporated and reconstituted in 100 μl of benzene to be assayed for I by GLC with electron capture detection with a sensitivity of 5 ng/0.5 ml of biological fluid. The procedure was applied to pharmacokinetics in the dog and a two-compartment body model was observed with a terminal half-life of 103-130 min. At the 40mg dose, 60-40% was excreted renally unchanged and 20-34% as unidentified metabolites. At the 200-mg dose 82-85% was excreted renally unchanged and 15-17% as unidentified metabolites. The respective renal clerances of I were 135 and 163 ml/min. The respective total clearances of I were 204 and 191 ml/min. These metabolites were apparently unextracted with chloroform from biological fluids at pH 11 and the liquid scintillation counting (LSC) assay of extracted radiolabeled I appeared synonomous with the GLC assay of I in such fluids.
Visible-Light-Mediated Oxidative Debenzylation Enables the Use of Benzyl Ethers as Temporary Protecting Groups
Cavedon, Cristian,Sletten, Eric T.,Madani, Amiera,Niemeyer, Olaf,Seeberger, Peter H.,Pieber, Bartholom?us
supporting information, p. 514 - 518 (2021/01/26)
The cleavage of benzyl ethers by catalytic hydrogenolysis or Birch reduction suffers from poor functional group compatibility and limits their use as a protecting group. The visible-light-mediated debenzylation disclosed here renders benzyl ethers temporary protective groups, enabling new orthogonal protection strategies. Using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as a stoichiometric or catalytic photooxidant, benzyl ethers can be cleaved in the presence of azides, alkenes, and alkynes. The reaction time can be reduced from hours to minutes in continuous flow.
Method for synthesizing release type xylose ester perfume for tobacco perfuming
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Paragraph 0026-0028; 0041-0043; 0056-0058, (2021/10/27)
A synthesis method of a release type xylose ester spice for flavoring tobacco is provided. The glucose is used as a raw material, the principle of esterifying carboxylic acid and alcohol to prepare ester is adopted, a common parent carboxylic acid which c