16096-98-3

Usage

Uses

Used in Organic Synthesis:
(4S,5S)-dithiane-4,5-diol is used as a protective group for aldehydes and ketones in organic synthesis, providing a means to protect these functional groups during chemical reactions and later deprotect them when needed.
Used in Pharmaceutical Industry:
(4S,5S)-dithiane-4,5-diol is used as a building block for the preparation of biologically active compounds, contributing to the development of new drugs and therapeutic agents.
Used in Chemical Research:
(4S,5S)-dithiane-4,5-diol is used as a research tool in the study of complex organic molecules, allowing scientists to explore its unique stereochemistry and reactivity in various chemical reactions.

InChI:InChI=1/C4H8O2S2/c5-3-1-7-8-2-4(3)6/h3-6H,1-2H2/t3-,4-/m0/s1

Upstream product

• 27565-41-9 1,4-dithio-D,L-threitol 
• 1077-28-7 Thioctic acid 
• 3483-12-3 DL-dithiothreitol 
• 3483-12-3 D,L-dithiothreitol 
• 6892-68-8 1,4-dithio-erythritol 
• 111807-83-1 4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro<1,2-dioxetane-3,2'-adamantane> 
• 62671-38-9 bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide 
• 145627-03-8 N,N'-Dicarbethoxy-N,N'-bis(mercaptomethyl)hydrazine Disulfide 
• 145626-94-4 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine Disulfide 
• 145626-99-9 N,N'-Bis(2-mercaptoacetyl)hexahydropyridazine Disulfide 
• 145627-07-2 1,2-Bis(mercaptomethyl)-4-methylurazole Disulfide 
• 145626-93-3 Bis(2-mercaptoethyl) Sulfone Disulfide 
• 27025-41-8 glutathione disulfide 
• 131760-68-4 1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane 

Downstream Products

• 27565-41-9 1,4-dithio-D,L-threitol 
• 131760-68-4 1,2-dimethyl-3,8-dioxo-1,2,5,6-diazadithiocane 
• 27025-41-8 glutathione disulfide 
• 145626-93-3 Bis(2-mercaptoethyl) Sulfone Disulfide 
• 145627-07-2 1,2-Bis(mercaptomethyl)-4-methylurazole Disulfide 
• 145626-99-9 N,N'-Bis(2-mercaptoacetyl)hexahydropyridazine Disulfide 
• 145627-03-8 N,N'-Dicarbethoxy-N,N'-bis(mercaptomethyl)hydrazine Disulfide 
• 145626-94-4 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine Disulfide 
• 3483-12-3 D,L-dithiothreitol 
• 39594-02-0 1,2-dithiane-t-4,c-5-diol r-1-oxide 
• 39594-02-0 1,2-dithiane-c-4,t-5-diol r-1-oxide 

Relevant academic research and scientific papers

Selective, Modular Probes for Thioredoxins Enabled by Rational Tuning of a Unique Disulfide Structure Motif

Specialized cellular networks of oxidoreductases coordinate the dithiol/disulfide-exchange reactions that control metabolism, protein regulation, and redox homeostasis. For probes to be selective for redox enzymes and effector proteins (nM to μM concentrations), they must also be able to resist non-specific triggering by the ca. 50 mM background of non-catalytic cellular monothiols. However, no such selective reduction-sensing systems have yet been established. Here, we used rational structural design to independently vary thermodynamic and kinetic aspects of disulfide stability, creating a series of unusual disulfide reduction trigger units designed for stability to monothiols. We integrated the motifs into modular series of fluorogenic probes that release and activate an arbitrary chemical cargo upon reduction, and compared their performance to that of the literature-known disulfides. The probes were comprehensively screened for biological stability and selectivity against a range of redox effector proteins and enzymes. This design process delivered the first disulfide probes with excellent stability to monothiols yet high selectivity for the key redox-Active protein effector, thioredoxin. We anticipate that further applications of these novel disulfide triggers will deliver unique probes targeting cellular thioredoxins. We also anticipate that further tuning following this design paradigm will enable redox probes for other important dithiol-manifold redox proteins, that will be useful in revealing the hitherto hidden dynamics of endogenous cellular redox systems.

Oxidative Formation of Disulfide Bonds by a Chemiluminescent 1,2-Dioxetane under Mild Conditions

The oxidation of alkyl thiols to disulfides has been achieved under mild conditions using a chemiluminescent 1,2-dioxetane as a stoichiometric oxidant. Besides the mild and biocompatible reaction conditions, this approach offers the possibility to monitor the presence of thiols through oxidation and chemiluminescence of the remaining dioxetane.

Syntheses of prodrug-type phosphotriester oligonucleotides responsive to intracellular reducing environment for improvement of cell membrane permeability and nuclease resistance

We synthesized prodrug-type phosphotriester (PTE) oligonucleotides containing the six-membered cyclic disulfide moiety by using phosphoramidite chemistry. Prodrug-type oligonucleotides named “Reducing-Environment-Dependent Uncatalyzed Chemical Transforming (REDUCT) PTE oligonucleotides” were converted into natural oligonucleotides under cytosol-mimetic reductive condition. Furthermore, the REDUCT PTE oligonucleotides were robust to nuclease digestion and exhibited good cell membrane permeability.

Hydrogen Bonding-Assisted Enhancement of the Reaction Rate and Selectivity in the Kinetic Resolution of d,l-1,2-Diols with Chiral Nucleophilic Catalysts

An extremely efficient acylative kinetic resolution of d,l-1,2-diols in the presence of only 0.5 mol% of binaphthyl-based chiral N,N-4-dimethylaminopyridine was developed (selectivity factor of up to 180). Several key experiments revealed that hydrogen bonding between the tert-alcohol unit(s) of the catalyst and the 1,2-diol unit of the substrate is critical for accelerating the rate of monoacylation and achieving high enantioselectivity. This catalytic system can be applied to a wide range of substrates involving racemic acyclic and cyclic 1,2-diols with high selectivity factors. The kinetic resolution of d,l-hydrobenzoin and trans-1,2-cyclohexanediol on a multigram scale (10 g) also proceeded with high selectivity and under moderate reaction conditions: (i) very low catalyst loading (0.1 mol%); (ii) an easily achievable low reaction temperature (0 °C); (iii) high substrate concentration (1.0 M); and (iv) short reaction time (30 min). (Figure presented.).

Tris(3-hydroxypropyl)phosphine (THPP): A mild, air-stable reagent for the rapid, reductive cleavage of small-molecule disulfides

Tris(3-hydroxypropyl)phosphine (THPP) is demonstrated to be a versatile, water-soluble and air-stable reducing agent, allowing for the rapid, irreversible reductive cleavage of disulfide bonds in both aqueous and buffered aqueous-organic media. The reagent shows exceptional stability at biological pH under which condition it permits the rapid reduction of a wide range of differentially functionalized small-molecule disulfides.

A potent, versatile disulfide-reducing agent from aspartic acid

Dithiothreitol (DTT) is the standard reagent for reducing disulfide bonds between and within biological molecules. At neutral pH, however, >99% of DTT thiol groups are protonated and thus unreactive. Herein, we report on (2S)-2-amino-1,4-dimercaptobutane (dithiobutylamine or DTBA), a dithiol that can be synthesized from l-aspartic acid in a few high-yielding steps that are amenable to a large-scale process. DTBA has thiol pKa values that are ～1 unit lower than those of DTT and forms a disulfide with a similar E o′ value. DTBA reduces disulfide bonds in both small molecules and proteins faster than does DTT. The amino group of DTBA enables its isolation by cation-exchange and facilitates its conjugation. These attributes indicate that DTBA is a superior reagent for reducing disulfide bonds in aqueous solution.

1,3-Dibromo-5,5-dimethylhydantoin [DBDMH] as an efficient and selective agent for the oxidation of thiols to Disulfides in solution or under solvent-free conditions

A useful method for oxidation of various thiols to their corresponding disulfides with 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) in very short reaction times and mild conditions under both solution and solvent-free conditions is described.

Silica phosphoric acid/NaNO2 as a novel heterogeneous system for the coupling of thiols to their corresponding disulfides

Silica phosphoric acid was prepared via reaction of silica chloride (I) and phosphoric acid. Thiols can be readily converted to their corresponding thionitrites with a combination of silica phosphoric acid (II), wet SiO 2, and sodium nitrite in dichloromethane at room temperature. Disulfides result from the homolytic cleavage of the sulfur-nitrogen bond of the unstable thionitrite and subsequent coupling of the resultant thiyl radicals.

dl-biTOT - A novel building block for electroactive oligomers and polymers in semiconductor applications

The title compound dl-biTOT (1, dl-2,2′,3,3′-tetrahydro2,2′-bithieno[3,2-b][1,4]oxathiine) was prepared in a five-step synthesis using cheap and readily available starting materials, with an overall yield of 50%. Compound 1 is believed to display interesting and unique properties as a building block in oligomer and polymer applications in the rapidly growing field of organic semiconductors. A new and superior method to oxidize dithiothreitol (Cleland's reagent), that operates rapidly and cleanly on a multigram scale is also reported.

Oxidation of thiols to disulfides with molecular bromine on hydrated silica gel support

Results of oxidation of thiols to disulfides with molecular bromine on silica gel solid support are reported. The procedure utilizes organic media and does not require a base to neutralize HBr by-products to suppress acid promoted side reactions. Utilization of silica gel support simplifies work up and product isolation.