38279-61-7

Basic information

• Product Name: [(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate
• CAS NO: 38279-61-7
• Molecular Formula: C₉H₁₈O₈S₂
• Molecular Weight: 318.3644
• Mol File: 38279-61-7.mol

Chemical Properties

• Boiling Point: 501.1°C at 760 mmHg
• Flash Point: 256.9°C
• Density: 1.331g/cm³
• Vapor Pressure: 1.11E-09mmHg at 25°C
• Refractive Index: 1.466
• CAS DataBase Reference: [(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate(CAS DataBase Reference)
• NIST Chemistry Reference: [(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate(38279-61-7)
• EPA Substance Registry System: [(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate(38279-61-7)

Safety Data

• Hazardous Substances Data: 38279-61-7(Hazardous Substances Data)

Usage

Uses

Used in Adhesives and Coatings Industry:
DDDS is used as a crosslinking agent for [enhancing the strength and durability of adhesives and coatings] because of its ability to create strong bonds and provide resistance to high temperatures and chemicals.
Used in Electronics Industry:
In the electronics industry, [(4R,5S)-2,2-dimethyl-1,3-dioxolane-4,5-diyl]dimethanediyl dimethanesulfonate is used as a curing agent for epoxy resins for [ensuring the stability and performance of electronic components] due to its high-temperature and chemical-resistant properties.
Used in Aerospace Industry:
Similarly, DDDS is utilized as a curing agent for epoxy resins in the aerospace industry to [maintain the structural integrity and reliability of aircraft components], capitalizing on its robust crosslinking capabilities and resistance to harsh environmental conditions.
Safety Precautions:

Upstream product

• 213767-09-0 2,3-O-isopropylidene-L-erythrofuranose 
• 71806-86-5 (4R,5S)-4,5-bis((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 
• 70789-54-7 meso-1,4-di-O-benzoyl-2,3-O-isopropylidenebutane-1,2,3,4-tetrol 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 124-63-0 methanesulfonyl chloride 
• 25432-12-6 2,3-O-Isopropyliden-DL-threitol 
• 116499-08-2 dimethyl 2,2-dimethyl-1,3-dioxolane-trans-4,5-dicarboxylate 

Downstream Products

• 213598-45-9 3,4-isopropylidenedioxy-Δ¹-pyrroline-1-oxide 
• 152139-64-5 (meso)-3,4-isopropylidenedioxy-2,5-pyrrolidine hydrotosylate 
• 151948-15-1 (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 13308-13-9 1,4-Di-O-methansulfonylerythrit 
• 299-74-1 DL-Threitol-1,4-bis-methansulfonat 

Relevant articles and documents

Effects of ring size and polar functional groups on the glutathione peroxidase-like antioxidant activity of water-soluble cyclic selenides

To elucidate the effects of ring structure and a substituent on the glutathione peroxidase- (GPx-) like antioxidant activities of aliphatic selenides, series of water-soluble cyclic selenides with variable ring size and polar functional groups were synthesized, and their antioxidant activities were evaluated by NADPH-coupled assay using H2O2 and glutathione (GSH) in water and also by NMR spectroscopy using H2O2 and dithiothreitol (DTTred) in methanol. Strong correlations were found among the GPx-like activity in water, the second-order rate constants for the oxidation of the selenides, and the HOMO energy levels calculated in water. The results support the conclusion that the oxidation process is the rate-determining step of the catalytic cycle. On the other hand, such correlations were not obtained for the activity observed in methanol. The optimal ring size was determined to be five. The type of substituent (NH2 2H) and the number can also control the activity, whereas the stereoconfiguration has only marginal effects on the activity in water. In methanol, however, the activity rank could not be explained by the simple scenarios applicable in water.

Combination of chemotherapy and oxidative stress to enhance cancer cell apoptosis

Cancer cells are vulnerable to reactive oxygen species (ROS) due to their abnormal redox environment. Accordingly, combination of chemotherapy and oxidative stress has gained increasing interest for the treatment of cancer. We report a novel seleno-prodrug of gemcitabine (Gem), Se-Gem, and evaluated its activation and biological effects in cancer cells. Se-Gem was prepared by introducing a 1,2-diselenolane (a five-membered cyclic diselenide) moiety into the parent drug Gemvia a carbamate linker. Se-Gem is preferably activated by glutathione (GSH) and displays a remarkably higher potency than Gem (up to a 6-fold increase) to a panel of cancer cell lines. The activation of Se-Gem by GSH releases Gem and a seleno-intermediate nearly quantitatively. Unlike the most ignored side products in prodrug activation, the seleno-intermediate further catalyzes a conversion of GSH and oxygen to GSSG (oxidized GSH) and ROS via redox cycling reactions. Thus Se-Gem may be considered as a suicide agent to deplete GSH and works by a combination of chemotherapy and oxidative stress. This is the first case that employs a cyclic diselenide in prodrug design, and the success of Se-Gem as well as its well-defined action mechanism demonstrates that the 1,2-diselenolane moiety may serve as a general scaffold to advance constructing novel therapeutic molecules with improved potency via a combination of chemotherapy and oxidative stress.

A novel method for the synthesis of 4'-thiopyrimidine nucleosides using hypervalent iodine compounds.

The coupling reactions of cyclic sulfides with a silylated pyrimidine nucleobase using a hypervalent iodine reagent were investigated. The reaction of silylated uracil with cyclic sulfide 12 using PhI=O gave the desired beta-anomer 14 in moderate yield. 4

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

Nucleosides and nucleotides. 189. Investigation of the stereoselective coupling of thymine with meso-thiolane-3,4-diol-1-oxide derivatives via the Pummerer reaction

We investigated the stereoselective coupling of thymine with sulfoxides derived from mesothiolane-3,4-diol via the Puremeter reaction. The introduction of 2,4-dimethoxybenzoyl groups to the hydroxyl groups of meso- thiolane-3,4-diol-1-oxide was effective

Synthesis of trihydroxylated pyrrolizidines and indolizidines using cycloaddition reactions of functionalized cyclic nitrones, and the synthesis of (+)- and (-)-lentiginosine

Cycloadditions of 3,4-isopropylidenedioxy-Δ1-pyrroline-1-oxide (9), (3S,4S)-3,4-bis(methoxy-methoxy)-Δ1-pyrroline-N-oxide (28), and its (3R, 4R)-enantiomer, with suitably-functionalized alkenes has led to the synthesis of the 1,2,6-trihydroxypyrrolizidines 14, 33 and ent-33, and the 1,2,7- trihydroxyindolizidines 22, 39 and ent-39. Deoxygenation of two enantiomeric intermediates in these syntheses led to the preparation of the dihydroxylated indolizidine (+)-lentiginosine and its (-)-enantiomer.

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.