4351-11-5

Usage

Uses

Used in Organic Synthesis:
4-Iodomethyl-2,2-dimethyl-[1,3]dioxolane is used as a reagent in organic synthesis for the creation of a wide range of functionalized molecules. Its unique structure allows for the formation of new chemical bonds and the synthesis of complex organic compounds.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, 4-Iodomethyl-2,2-dimethyl-[1,3]dioxolane serves as a building block for the development of new drugs. Its ability to form various functionalized molecules makes it a valuable component in the synthesis of pharmaceutical compounds with potential therapeutic applications.
Used in Materials Science:
4-Iodomethyl-2,2-dimethyl-[1,3]dioxolane has potential applications in the field of materials science, particularly in the production of polymers and specialty chemicals. Its unique properties and reactivity contribute to the development of innovative materials with specific characteristics and functionalities.
Used in Research and Development:
4-IODOMETHYL-2,2-DIMETHYL-[1,3]DIOXOLANE is also utilized in research and development settings, where it can be employed to explore new chemical reactions, investigate its reactivity, and study its potential applications in various fields.
It is crucial to handle 4-Iodomethyl-2,2-dimethyl-[1,3]dioxolane with care due to its potential health and environmental hazards. Proper safety measures should be taken during its synthesis, storage, and use to minimize any risks associated with this chemical compound.

InChI:InChI=1/C6H11IO2/c1-6(2)8-4-5(3-7)9-6/h5H,3-4H2,1-2H3/t5-/m0/s1

Upstream product

• 554-10-9 3-iodo-propane-1,2-diol 
• 67-64-1 acetone 
• 17579-99-6 methyltriphenoxyphosphonium iodide 
• 100-79-8 (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol 
• 23737-51-1 solketal tosylate 
• 34832-91-2 1,2-O-isopropylideneglyceryl N,N,N'N,-tetraethylphosphorodiamidite 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 83461-40-9 methanesulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 

Downstream Products

• 82954-65-2 [(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]methanamine 
• 85820-82-2 (S)-1-azido-1-deoxy-2,3-O-isopropylidene-glycerol 
• 779352-55-5 2-[2-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-4,4-dimethyl-4,5-dihydro-oxazole 

Relevant academic research and scientific papers

Discovery of 2-Sulfinyl-Diazabicyclooctane Derivatives, Potential Oral β-Lactamase Inhibitors for Infections Caused by Serine β-Lactamase-Producing Enterobacterales

Coadministration of β-lactam and β-lactamase inhibitor (BLI) is one of the well-established therapeutic measures for bacterial infections caused by β-lactam-resistant Gram-negative bacteria, whereas we have only two options for orally active BLI, clavulanic acid and sulbactam. Furthermore, these BLIs are losing their clinical usefulness because of the spread of new β-lactamases, including extended-spectrum β-lactamases (ESBLs) belonging to class A β-lactamases, class C and D β-lactamases, and carbapenemases, which are hardly or not inhibited by these classical BLIs. From the viewpoints of medical cost and burden of healthcare personnel, oral therapy offers many advantages. In our search for novel diazabicyclooctane (DBO) BLIs possessing a thio-functional group at the C2 position, we discovered a 2-sulfinyl-DBO derivative (2), which restores the antibacterial activities of an orally available third-generation cephalosporin, ceftibuten (CTB), against various serine β-lactamase-producing strains including carbapenem-resistant Enterobacteriaceae (CRE). It can be orally absorbed via the ester prodrug modification and exhibits in vivo efficacy in a combination with CTB.

Design, Synthesis, and Preliminary Immunological Studies of MUC1-Based Antitumor Vaccines Adjuvanted with R- And S-FSL-1

Fibroblast stimulating lipopeptide 1 (FSL-1) is the ligand of TLR2 and TLR6 and can be used as the vaccine adjuvant to prepare antitumor vaccines. However, FSL-1 is a stereoisomeric mixture that contains the R stereoisomer and S stereoisomer, and it is still unclear which stereoisomer has better adjuvant activities. In this work, we designed and synthesized MUC1-based antitumor vaccines adjuvanted with the stereoisomers R-FSL-1 and S-FSL-1, which were synthesized from the stereoisomeric building blocks R-Fmoc-Pam2Cys-OH and S-Fmoc-Pam2Cys-OH, respectively. Immunological evaluation indicated that both R-FSL-1 and S-FSL-1 can be used as adjuvants for the construction of MUC1-based antitumor vaccines, with R-FSL-1 showing a better adjuvant effect than S-FSL-1.

Design and preparation of a novel prolinamide-based organocatalyst for the solvent-free asymmetric aldol reaction

The preparation of four novel organocatalysts as highly diastereo and enantioselective catalysts for the solvent-free asymmetric aldol reaction was described. These organocatalysts were synthesized in eight steps applying simple and commercially available starting materials. The best results were obtained for the proline-derived catalyst, providing access to the desired adducts in up to 95% yield, 1:19 syn/anti and 98% e.e. Moreover, even sterically bulky aldehydes and substituted cyclohexanones were well tolerated. DFT calculations and control experiments indicated that several hydrogen bonding interactions between the aldehyde and the enamine intermediate are responsible for the stereoselective chiral induction process and that the trifluoroacetate counter-anion is crucial for the attainment of higher stereoselectivities.

Amino acid ionic liquids as catalysts in a solvent-free Morita-Baylis-Hillman reaction

In the present work, we describe the preparation of ten amino acid ionic liquids (AAILs) formed from ammonium salts as cations, derivatives of glycerol, and natural amino acids as anions. All of them are viscous oils, colorless or pale yellow, and hygroscopic at room temperature. They have appreciable solubility in many protic and aprotic polar solvents. The AAILs were used as catalysts in a Morita-Baylis-Hillman (MBH) reaction. The ionic liquids derivative from l-proline and l-histidine demonstrated the ability to catalyze the reaction between methyl vinyl ketone and aromatic aldehydes differently substituted in the absence of an additional co-catalyst under organic solvent-free conditions. The AAIL derivatives from l-valine, l-leucine, and l-tyrosine catalyzed the MBH reaction only in the presence of imidazole. The MBH adducts were obtained in moderate to good yields. Although the catalytic site in the ILs was in its enantiomerically pure form, all the MBH adducts were obtained in their racemic form.

An efficient and scalable synthesis of potent TLR2 agonistic PAM2CSK4

Diacylated PAM2CSK4, a highly expensive lipopeptide with desirable aqueous solubility and a broad spectrum of cytokine/chemokine induction is a most potent dual (human and murine) Toll-Like Receptor-2 (TLR2) agonist. Besides such thrilling characteristics, its synthetic process is not reported in the literature. The present report describes an efficient and scalable 20 step synthesis of PAM2CSK4 in good yield (all steps > 60%) along with a clear description of the hindrances and easy solutions adopted in each step. Overall, a convergent synthetic approach was adopted involving synthesis of appropriately protected starting materials, synthesis of a key backbone skeleton PAM2CS, synthesis of a tetralysine fragment and the final coupling to yield PAM2CSK4. Tedious column chromatography was avoided on a large scale in many steps.

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

The present invention relates to a conjugated compound of Formula I : Q-Z-R4 wherein Q is a TLR7 and/or TLR8 agonist and Z-R4 is a TLR2 agonist, said conjugated compound being chosen among compounds of Formula II :

Conjugated TLR7 and/or TLR8 and TLR2 polycationic agonists

A conjugated compound of Formula I: Q-Z—R4 wherein Q is a TLR7 and/or TLR8 agonist and Z—R4 is a TLR2 agonist, the conjugated compound being chosen among compounds of Formula II:

CONJUGATED TLR7 AND/OR TLR8 AND TLR2 AGONISTS

A conjugated compound of formula Q-Z—R4 wherein Q is a TLR7 and/or TLR8 agonist and Z—R4 is a TLR2 agonist, and the uses thereof in the treatment of infection, cancer or immune disorders or for use in vaccines.

Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors

Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-d-myo-inositol-1-O-(sn-3,4- bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-d- glucopyranosyl)-d-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1- phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with phosphonic acids 18a and 18b respectively in quantitative yield followed by de-protection. These synthetic C-phosphonate GPI-probes were resistant to phosphatidylinositol specific phospholipase C (PI-PLC) and also showed moderate inhibition of the enzyme activity. The Royal Society of Chemistry.