151948-15-1

Basic information

• Product Name: (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole
• CAS NO: 151948-15-1
• Molecular Weight: 233.31
• Mol File: 151948-15-1.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole(151948-15-1)
• EPA Substance Registry System: (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole(151948-15-1)

Safety Data

• Hazardous Substances Data: 151948-15-1(Hazardous Substances Data)

Upstream product

• 146566-82-7 (4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-dicarbaldehyde 
• 100-46-9 benzylamine 
• 67814-68-0 2,3-O-isopropylidene-D-ribofuranose 
• 1028903-71-0 N-benzyl-(3S,4R)-3,4-dihydroxy-2,5-pyrrolidinedione 
• 1631-26-1 1-benzyl-1H-pyrrole-2,5-dione 
• 38279-61-7 meso-2,3-O-isopropylidene-1,4-di-O-(methanesulfonyl)butane-1,2,3,4-tetrol 
• 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 

Downstream Products

• 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 
• 213598-45-9 3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide 

Relevant articles and documents

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).

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.

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.