23735-44-6

Usage

Uses

Used in Pharmaceutical Industry:
2,2-DIMETHYL-4(S)-4-IODOMETHYL-1,3-DIOXALANE is used as a reagent and building block for the synthesis of pharmaceuticals. Its unique structure and stereochemistry make it a valuable component in the development of new drugs, contributing to the creation of molecules with specific therapeutic properties.
Used in Agrochemical Industry:
In the agrochemical sector, 2,2-DIMETHYL-4(S)-4-IODOMETHYL-1,3-DIOXALANE is employed as a building block in the synthesis of agrochemicals. Its role in the production of pesticides, herbicides, and other agricultural chemicals is crucial for enhancing crop protection and yield.
Used in Specialty Chemicals Industry:
2,2-DIMETHYL-4(S)-4-IODOMETHYL-1,3-DIOXALANE is utilized as a building block in the synthesis of specialty chemicals. Its versatility in chemical reactions allows for the production of a wide range of chemical products with specific applications in various industries.
Used in Natural Product Synthesis:
2,2-DIMETHYL-4(S)-4-IODOMETHYL-1,3-DIOXALANE is also used as a building block in the synthesis of complex natural products. Its ability to contribute to the formation of intricate molecular structures makes it an essential tool in the replication and modification of naturally occurring substances.
Used in Biologically Active Molecules Synthesis:
2,2-DIMETHYL-4(S)-4-IODOMETHYL-1,3-DIOXALANE is employed as a chiral building block for the synthesis of biologically active molecules. Its stereochemistry plays a critical role in determining the reactivity and selectivity of the molecules, which is essential for their biological activity and potential therapeutic applications.

InChI:InChI=1/C6H11IO2/c1-6(2)8-4-5(3-7)9-6/h5H,3-4H2,1-2H3/t5-/m1/s1

Upstream product

• 23735-43-5 (S)-1-O-tosyl-2,3-O-isopropylideneglycerol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 

Downstream Products

• 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.

An easy and versatile approach to the synthesis of chiral pheromone lactones via 4,4-dimethyl-2-oxazoline derivatives

As part of our ongoing investigation on the versatility of 4,4-dimethyl-2-oxazoline derivatives, we present a straightforward synthesis of chiral lactone pheromones from readily available starting materials. As an application, we describe the diastereoselective synthesis of cis and trans-2-methyl-5-hexanolide (1), a pheromone component of the carpenter bee Xylocopa hirutissima, and a formal synthesis of (4R,5Z)-5-tetradecen-4-olide (2), the sex pheromone of the Japanese beetle Popillia japonica.

Synthesis and antimuscarinic properties of some N-substituted 5- (aminomethyl)-3,3-diphenyl-2(3H)-furanones

In a study aimed toward developing new, selective antimuscarinic drugs with potential utility in the treatment of urinary incontinence associated with bladder muscle instability, a series of N-substituted 5-(aminomethyl)- 3,3-diphenyl-2(3H)-furanones, conformationally-constrained lactone relatives of benactyzine, was prepared. The compounds were examined in several paradigms that measure muscarinic (M1, M2, and M3) receptor antagonist activity. Selected members of the series that displayed potency and/or selectivity in these tests were studied for their effects on urinary bladder contraction, mydriasis, and salivation in guinea pigs. These studies revealed that incorporation of the amino functionality into an imidazole or pyrazole ring resulted in some novel, potent, and selective antimuscarinic agents. Appropriate alkyl substitution of position 2 of the imidazole strikingly affected muscarinic, particularly M3, receptor activity and may reflect a complementary site of interaction. Some of the compounds selectively reduced bladder pressure in a cystometrogram (CMG) model without producing concomitant mydriatic and salivary effects. The separate and distinct action of several compounds of this series in these in vivo protocols suggests the possibility of subtypes of muscarinic receptors that may correspond to previously characterized molecular cloned subpopulations. In this article, structure-activity relationships for the series of substituted lactones are discussed. These studies led to the identification of (R)-[(2-isopropyl-1H- imidazol-1-yl)methyl]-4,5-dihydro-3,3-diphenyl-2(3H)-furanone (23) as a clinical candidate for treating urinary bladder dysfunction.

5-(1-(IMIDAZOL)METHYL)-3,3-DISUBSTITUTED-2(3H)FURANONE DERIVATIVES

Furanone compounds and compositions having anticholinergic activity are described. The compounds have the formula: STR1 wherein: the dashed line indicates either the 4,5-unsaturated or the 4,5-dihydrofuranone ring;R 1 and R 2 may be the same or different and are hydrogen, thienyl, furanyl, or cycloalkyl (C. sub.3-C 6), benzyl, phenyl, substituted phenyl or substituted benzyl wherein the phenyl or benzyl group may be substituted with halogen, trifluoromethyl, lower alkyl, lower alkoxy or hydroxy;R. sub.3, R 4 and R 5 may be the same or different and are hydrogen, lower alkyl, lower alkyl substituted with a halogen, alkoxy, amino or carboxylic acid group, an alkyl or alkylene bridge between R 4 and R. sub.5 or R 3 and the ring N, trifluoromethyl, nitro, a cycloalkyl group containing 3 to 6 carbons, halogen, benzyl, phenyl, substituted phenyl or substituted benzyl, for which the substituents are the same as those set forth for R 1 and R 2 substituted benzyl or phenyl.R 6 in the dihydrofuranone series is hydrogen or lower alkyl.Also described are the pharmaceutically acceptable quaternary alkyl and acid addition salts of such compounds. The compounds are particularly useful in the treatment of neurogenic bladder disorder and chronic obstructive pulmonary diseases.

Bryostatins: The asymmetric synthesis of C1-C9 and C11-C16 fragments

The fragments C1-C9 19 and C11-C16 26 of the bryostatins are constructed in an enantioselective and highly diastereoselective fashion from respectively D-pantolactone (2) and L-erythrulose (3) as chiral template