1028903-73-2

Usage

Uses

Used in Pharmaceutical Industry:
(3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole is used as a compound with potential pharmaceutical applications due to its unique structure that could confer specific biological activities. Further research is required to fully understand its properties and explore its potential uses in drug development.

Upstream product

• 100-46-9 benzylamine 
• 1028903-71-0 N-benzyl-(3S,4R)-3,4-dihydroxy-2,5-pyrrolidinedione 
• 146566-82-7 (4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbaldehyde 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 213767-09-0 2,3-O-isopropylidene-L-erythrofuranose 
• 38279-61-7 meso-2,3-O-isopropylidene-1,4-di-O-(methanesulfonyl)butane-1,2,3,4-tetrol 

Downstream Products

• 213598-45-9 3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide 
• 1028903-74-3 4-(((3aR,6aS)-2,2-dimethyldihydro-3aH-[1,3]dioxolo[4,5-c]pyrrol-5(4H)-yl)sulfonyl)benzonitrile 
• 383417-91-2 meso-3,4-isopropylidenedioxypyrrolidine hydrotosylate 

Relevant academic research and scientific papers

Use of DOE for rapid development of a red-Al reduction process for the synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate

Statistical design of experiments (DOE) was used to rapidly optimize Red-Al reduction of an imide to produce, after deprotection and salt formation, 3,4-isopropylidenedioxypyr-rolidine hydrotosylate (1), an intermediate in the synthesis of Ingliforib. A Red-Al reduction process was successfully scaled to produce multikilogram quantities of 1, thus demonstrating a safer and more economical process. Further development resulted in an optimized procedure, which not only avoided borane reduction but also allowed the three-step procedure to be performed without isolation of the intermediates, solvent exchange, or distillation.

Hydroxylated pyrrolizidines and indolizidines; syntheses using cycloaddition reactions of functionalized cyclic nitrones

Cycloaddition reactions of functionalised Δ1-pyrroline-N-oxides have been used to prepare the hydroxylated pyrrolizidines 11 and 22, the indolizidine 16, and the iminoheptitol 12.

FUNCTIONALIZED HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compound-linker constructs and antibody-drug-conjugates of compounds of formula (I) that are useful as modulators of STING (Stimulator of Interferon Genes).

HETEROCYCLIC COMPOUNDS AS MODULATORS OF STIMULATOR OF INTERFERON GENES (STING)

The present invention relates to compounds of formula (I) and salts, stereoisomers, tautomers or N-oxides thereof that are useful as modulators of STING (Stimulator of Interferon Genes). The present invention further relates to the compounds of formula (I) for use as a medicament and to a pharmaceutical composition comprising said compounds.

Synthesis of N-Substituted Iminosugar Derivatives and Evaluation of Their Immunosuppressive Activities

It is important to find more effective and safer immunosuppressants, because clinically used immunosuppressive agents have significant side effects. A series of N-substituted iminosugar derivatives were designed and synthesized, and their immunosuppressive effects were evaluated by the CCK-8 assay. The results revealed that iminosugars 10 e and 10 i, that is, (3R,4S)-1-(4-heptyloxylphenylethyl)pyrrolidine-3,4-diol and (3R,4S)-1-[2-(2-chloro-4-(p-tolylthio)-phenyl-1-yl)ethyl]pyrrolidine-3,4-diol, respectively, exhibited the strongest inhibitory effects on mouse splenocyte proliferation (IC50=2.16 and 2.48 μm, respectively), whereas the iminosugars containing an amide group near the hydrophilic head (compounds 10 j–n) exhibited no inhibitory effects. Further studies revealed that the inhibitory effects on splenocyte proliferation may have come from the suppression of both IFN-γ and IL-4 cytokines. Our results suggest that synthetic iminosugars, especially compounds 10 e and 10 i, hold potential as immunosuppressive agents.

A methodology for simultaneous fluorogenic derivatization and boronate affinity enrichment of 3-nitrotyrosine-containing peptides

We synthesized and characterized a new tagging reagent, (3R,4S)-1-(4-(aminomethyl)phenylsulfonyl)pyrrolidine-3,4-diol (APPD), for the selective fluorogenic derivatization of 3-nitrotyrosine (3-NT) residues in peptides (after reduction to 3-aminotyrosine) and affinity enrichment. The synthetic 3-NT-containing peptide, FSAY(3-NO2)LER, was employed as a model for method validation. Furthermore, this derivatization protocol was successfully tested for analysis of 3-NT-containing proteins exposed to peroxynitrite in the total protein lysate of cultured C2C12 cells. The quantitation of 3-NT content in samples was achieved through either fluorescence spectrometry or boronate affinity chromatography with detection by specific fluorescence (excitation and emission wavelengths of 360 and 510 nm, respectively); the respective limits of detection were 95 and 68 nM (19 and 13 pmol total amount) of 3-NT. Importantly, the derivatized peptides show a strong retention on a synthetic boronate affinity column, containing sulfonamide-phenylboronic acid, under mild chromatographic conditions, affording a route to separate the derivatized peptides from large amounts (milligrams) of nonderivatized peptides and to enrich them for fluorescent detection and mass spectrometry (MS) identification. Tandem MS analysis identified chemical structures of peptide 3-NT fluorescent derivatives and revealed that the fluorescent derivatives undergo efficient backbone fragmentations, permitting sequence-specific identification of protein nitration at low concentrations of 3-NT in complex protein mixtures. Copyright

Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: Ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes

Representative diastereomeric, erythritol and threitol polyhydroxylated pyrrolidine imine scaffolds have been rapidly elaborated to diversely functionalized aza-sugars through highly diastereoselective organometallic (RM) additions (R = Me, Et, allyl, hex

Processes and intermediates for preparing glycogen phosphorylase inhibitors

The instant invention provides novel processes and intermediates useful in the preparation of certain N-(indole-2-carbonyl)-β-alaninamide compounds, which compounds are glycogen phosphorylase inhibitors useful in the treatment of diseases such as hypercholesterolemia, hyperglycemia, hyperinsulinemia, hyperlipidemia, hypertension, atherosclerosis, diabetes, diabetic cardiomyopathy, infection, tissue ischemia, myocardial ischemia, and in inhibiting tumor growth.

Practical large-scale synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate: Atom economical self-hydrogenolysis of a crystalline borane-benzylamine adduct

An efficient four-step sequence has been developed for the synthesis of 3,4-isopropylidenedioxypyrrolidine hydrotosylate starting from inexpensive N-benzylmaleimide. This approach features a novel N-debenzylation procedure that utilizes the corresponding

Palladium and Raney Nickel Catalyzed Methanolic Cleavage of Stable Borane-Amine Complexes

(Matrix Presented) Palladium and Raney nickel were found to catalyze the methanolysis of borane-amine adducts. Hence, strongly complexed amines can now be liberated by simple treatment with Pd/C or Raney Ni in methanol. The method is applicable to primary