23735-39-9

Usage

Uses

Used in Organic Synthesis:
2,2-DIMETHYL-4(R)-4-IODOMETHYL-1,3-DIOXALANE is used as a reagent in organic synthesis for the construction of complex organic molecules, serving as a building block in various chemical reactions.
Used in Pharmaceutical Research:
In pharmaceutical research, 2,2-DIMETHYL-4(R)-4-IODOMETHYL-1,3-DIOXALANE is utilized as a key component in the synthesis of new drug candidates, contributing to the development of innovative medications.
Used in Pharmaceutical Production:
2,2-DIMETHYL-4(R)-4-IODOMETHYL-1,3-DIOXALANE is employed in the production of pharmaceuticals, playing a crucial role in the manufacturing process of certain drugs.
Used in Agrochemical Production:
2,2-DIMETHYL-4(R)-4-IODOMETHYL-1,3-DIOXALANE is also used in the production of agrochemicals, where it may be involved in the synthesis of pesticides or other agricultural chemicals to improve crop protection and yield.
Safety Considerations:
2,2-DIMETHYL-4(R)-4-IODOMETHYL-1,3-DIOXALANE is considered potentially hazardous if mishandled due to its reactivity as a chemical compound. It should be handled with care in a controlled environment to ensure safety.

Upstream product

• 23788-74-1 (R)-2,2-dimethyl-1,3-dioxolane-4-ylmethyl p-toluenesulfonate 
• 83461-40-9 methanesulfonic acid (R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester 
• 22323-82-6 (S)-(+)-(2,2-dimethyl-[1,3]dioxolan-4-yl)methanol 
• 1707-77-3 1,2:5,6-di-O-isopropylidene-D-mannitol 
• 14347-78-5 1,2-O-isopropylidene-D-glycerol 
• 15186-48-8 2,3-isopropylidene-glyceraldehyde 

Downstream Products

• 144042-75-1 3-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-diphenyl-propionic acid 
• 396092-17-4 (5S)-5,6-(dimethylmethylene)dioxy-2-methylhex-1-en-3-yl phenyl sulfone 
• 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 
• 881993-61-9 C₁₆H₂₃NO₇S 
• 276238-64-3 2-benzenesulfonyl-3-(2,2-dimethyl-[1,3]dioxolan-4-yl)-N-methoxy-N-methyl-propionamide 
• 220133-88-0 (4S)-4-<2,2-bis(benzoxycarbonyl)ethyl>-2,2-dimethyl-1,3-dioxolane 

Relevant academic research and scientific papers

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.

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.

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.

Total synthesis of epothilones using functionalised allylstannanes for remote stereocontrol

Two syntheses of the C(7)-C(16)-fragment 41 of epothilone D 2 were developed that were based on tin(iv) bromide mediated reactions of 5,6-difunctionalised hex-2-enylstannanes with aldehydes. In the first synthesis, (5S)-6-tert-butyldimethylsilyloxy-5-hydroxy-2-methylhex-2-enyl(tributyl) stannane 20 was reacted with (E)-but-2-enal to give (2S,7R,4Z,8E)-1-tert- butyldimethylsilyloxy-5-methyldeca-4,8-diene-2,7-diol 26 containing ca. 20% of its (7S)-epimer. Following desilylation, the crystalline (2S,7R)-triol 32 was protected as its acetonide 33 and esterified to give the (4-methoxybenzyloxy) acetate 34. An Ireland-Claisen rearrangement of this ester gave methyl (2R,3S,10S,4E,7Z)-3,7-dimethyl-10,11-(dimethylmethylene)dioxy-2-(4- methoxybenzyloxy)undeca-4,7-dienoate 35 that was converted into (2S,9S,6Z)-2,6-dimethyl-9,10-(dimethylmethylene)dioxydec-6-en-1-ol 41 by regioselective alkene manipulation, ester reduction and cleavage of the resulting terminal diol 40 with a reductive work-up. The second synthesis involved the tin(iv) bromide mediated reaction between the stannane 20 and (3S)-4-(4-methoxybenzyloxy)-3-methylbutanal 44 that gave (2S,7S,9S,4Z)-1-tert- butyldimethylsilyloxy-5,9-dimethyl-10-(4-methoxybenzyloxy)dec-4-ene-2,7-diol 45 containing ca. 20% of its (7R)-epimer. After desilylation and protection of the vicinal diol as its acetonide 46, a Barton-McCombie reductive removal of the remaining hydroxyl group gave the (2S,9S,6Z)-2,6-dimethyl-9,10- (dimethylmethylene)dioxydec-6-en-1-ol 41 after oxidative removal of the PMB-ether. The first of these syntheses uses just one chiral starting material, but the second is shorter and more convergent. It was therefore modified by the use of (5S)-6-tert-butyldimethylsilyloxy-5-(2-trimethylsilylethoxy)methoxy-2- methylhex-2-enyl(tributyl)stannane 49 that reacted with (3S)-4-(4- methoxybenzyloxy)-3-methylbutanal 44 to give a 50:50 mixture of the C(4)-epimers of (2S,9S,6Z)-10-tert-butyldimethylsilyloxy-1-(4-methoxybenzyloxy)-2,6- dimethyl-9-(2-trimethylsilylethoxy)methoxydec-6-en-4-ol 50 with high fidelity for formation of the (Z)-alkene. Following the Barton-McCombie deoxygenation, the product 52 was taken through to (2S,9S,6Z,10E)-2,6,10-trimethyl-11-(2- methyl-1,3-thiazol-4-yl)-9-(2-trimethylsilylethoxy)methoxyundeca-6,10-dienal 59 that corresponded to the fully functionalised C(7)-C(17) fragment of epothilone D 2. A precedented stereoselective aldol condensation followed by O-protection, selective deprotection, oxidation and macrocyclisation then gave the macrolide 71 that was deprotected to complete a synthesis of epothilone D 2. Finally regio- and stereo-selective epoxidation gave epothilone B 1.

Structure-activity relationships in toll-like receptor-2 agonistic diacylthioglycerol lipopeptides

The N-termini of bacterial lipoproteins are acylated with a (S)-(2,3-bisacyloxypropyl)cysteinyl residue. Lipopeptides derived from lipoproteins activate innate immune responses by engaging Toll-like receptor 2 (TLR2) and are highly immunostimulatory and yet without apparent toxicity in animal models. The lipopeptides may therefore be useful as potential immunotherapeutic agents. Previous structure-activity relationships in such lipopeptides have largely been obtained using murine cells, and it is now clear that significant species-specific differences exist between human and murine TLR responses. We have examined in detail the role of the highly conserved Cys residue as well as the geometry and stereochemistry of the Cys-Ser dipeptide unit. (R)-Diacylthioglycerol analogues are maximally active in reporter gene assays using human TLR2. The Cys-Ser dipeptide unit represents the minimal part-structure, but its stereochemistry was found not to be a critical determinant of activity. The thioether bridge between the diacyl and dipeptide units is crucial, and replacement by an oxoether bridge results in a dramatic decrease in activity.

A short and versatile route to chiral spiroketal skeletons

Different chiral spiroketal skeletons are obtained, in a versatile manner, by iterative alkylations of acetone N,N-dimethylhydrazone with iodides 2 followed by a one-pot deprotection/spirocyclization sequence. This methodology has been applied successfull

Syntheses of 4-deoxy-D-fructose and enzymatic affinity study

Enantiomerically pure 4-deoxy-D-fructose has been prepared and characterised in a protected form, acidic hydrolysis of which led to an aqueous solution of 4-deoxy-D-fructose. Activities of this compound with enzymes of the glycolysis pathway involved in glucose metabolism make possible access to 4-deoxy-D-fructose-6-phosphate, 4-deoxy-D-glucose-6- phosphate and 4-deoxy-D-gluconate-6-phosphate.

Syntheses of L-threose and D-erythrose analogues modified at position 2

2-O-Methyl-D-erythrose, 2-O-methyl-L-threose, 2-deoxy-D- and L- erythrose, and the corresponding acetonides have been prepared from the commercially available D-isoascorbic and L-ascorbic acids. The proportion of cyclic (α and β furanoses) and acyclic (aldehyde and hydrate) forms was determined in aqueous (D2O) solution by 1H and 13C NMR spectroscopy.

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.