40227-25-6

Basic information

• Product Name: (4R,5S)-1,2-Dithiane-4,5-diol
• Synonyms: (4R,5S)-1,2-Dithiane-4,5-diol
• CAS NO: 40227-25-6
• Molecular Formula: C₄H₈O₂S₂
• Molecular Weight: 152.24
• Mol File: 40227-25-6.mol
• Article Data: 22

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4R,5S)-1,2-Dithiane-4,5-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (4R,5S)-1,2-Dithiane-4,5-diol(40227-25-6)
• EPA Substance Registry System: (4R,5S)-1,2-Dithiane-4,5-diol(40227-25-6)

Safety Data

• Hazardous Substances Data: 40227-25-6(Hazardous Substances Data)

Usage

Description

(4R,5S)-1,2-Dithiane-4,5-diol is a chemical compound with the molecular formula C4H10O2S2, characterized as a diol with two hydroxyl groups and a derivative of dithiane, featuring a five-membered ring with two sulfur atoms. (4R,5S)-1,2-Dithiane-4,5-diol is known for its applications in organic synthesis and potential pharmaceutical uses.

Uses

Used in Organic Synthesis:
(4R,5S)-1,2-Dithiane-4,5-diol is used as a protecting group for carbonyl compounds, such as aldehydes and ketones, in the field of organic synthesis. It forms a dithioacetal with the carbonyl group, preventing unwanted reactions and enabling selective manipulation of the target molecule.
Used in Pharmaceutical Applications:
(4R,5S)-1,2-Dithiane-4,5-diol is also studied for its potential use in the pharmaceutical industry, where it may contribute to the development of new drugs and therapies.
Used as a Chiral Building Block:
In the synthesis of complex molecules, (4R,5S)-1,2-Dithiane-4,5-diol serves as a chiral building block, playing a crucial role in the creation of enantiomerically pure compounds, which are essential in various chemical and pharmaceutical applications.

Upstream product

• 27565-41-9 1,4-dithio-D,L-threitol 
• 1077-28-7 Thioctic acid 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 
• 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 
• 145626-94-4 N,N'-Dicarbomethoxy-N,N'-bis(mercaptomethyl)ethylenediamine Disulfide 
• 145627-03-8 N,N'-Dicarbethoxy-N,N'-bis(mercaptomethyl)hydrazine Disulfide 
• 62671-38-9 bis (1-methyl-(1H)-tetrazol-5-yl)-disulfide 
• 3483-12-3 D,L-dithiothreitol 
• 111807-83-1 4-(3-tert-butyldimethylsilyloxyphenyl)-4-methoxyspiro<1,2-dioxetane-3,2'-adamantane> 
• 3483-12-3 DL-dithiothreitol 

Downstream Products

• 3483-12-3 1,4-Dithioerythritol 
• 27565-41-9 1,4-dithio-D,L-threitol 
• 1077-28-7 Thioctic acid 
• 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 
• 1892-29-1 bis(2-hydroxyethyl) disulfide 

Relevant articles and documents

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.

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.

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.