671809-10-2

Usage

Uses

Used in Chemical Synthesis:
(3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL serves as a reactive intermediate for chemical synthesis, particularly in the creation of new compounds through its azide groups. The reactivity allows for a wide range of chemical transformations, making it valuable for the development of novel molecules with specific properties.
Used in Materials Science:
In the field of materials science, (3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL can be utilized to develop new materials with unique characteristics. (3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL's reactivity and functional groups can be leveraged to create materials with tailored properties for specific applications.
Used in Medicinal Chemistry Research:
(3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL holds promise in medicinal chemistry research for the design and synthesis of new pharmaceutical agents. Its reactive azide groups can be used to create bioactive molecules with potential therapeutic applications.
Used in Safety and Handling Protocols Development:
Due to the compound's high reactivity and potential safety concerns, (3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL is also used in the development of safety and handling protocols. Establishing proper procedures for its use ensures the safety of researchers and the integrity of experiments involving (3R,4R,6R)-5-AZIDO-2-AZIDOMETHYL-6-((1S,2S,4S)-4,6-DIAZIDO-2,3-DIHYDROXY-CYCLOHEXYLOXY)-TETRAHYDRO-PYRAN-3,4-DIOL.

Upstream product

• 67-56-1 methanol 
• 1268528-26-2 pentaazidokanamycin B 
• 182554-04-7 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine 
• 474266-81-4 hexaazido-hepta-O-acetyl neomycin 
• 468065-21-6 hexaazidoneomycin B 
• 119-04-0 neomycin B 
• 41547-94-8 4-O-(2,6-di-deoxy-α-D-2,6-di-amine-glucopyranosyl)-2-deoxy-streptamine hydrochloride 
• 3855-45-6 triflic azide 
• 3947-65-7 neomycin A 
• 25389-98-4 neomycin B sulphate 
• 15446-43-2 neamine tetrahydrochloride 

Downstream Products

• 182554-04-7 1,3,2′,6′-tetraazido-6,3′,4′-tri-O-acetylneamine 
• 182554-06-9 5,6,3',4'-tetra-O-acetyl-1,3,2',6'-tetrazidoneamine 
• 786701-91-5 (2R,3R,4R,5R,6R)-3-Azido-6-azidomethyl-2-((1R,2R,3S,4R,6S)-4,6-diazido-2,3-dimethoxy-cyclohexyloxy)-4,5-dimethoxy-tetrahydro-pyran 
• 671809-11-3 C₃₃H₃₀N₁₂O₉ 
• 688744-66-3 1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine 

Relevant academic research and scientific papers

An alternative and facile synthetic approach for the precursors of 3- and 6-aminosugar donors and study of one-pot glycosyltrasferation

3- and 6-aminosugars are common motifs in bioactive compounds playing pivotal roles in the bioactivity of the core molecules to which they are attached. However, de novo synthesis of 3- and 6-aminosugars and their corresponding glycosyl donors can be time

Synthesis of glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B and their effect on RNA and DNA triplex stability

Glycosidic (β-1′′→6, 3′ and 4′) site isomers of neomycin B (i.e., neobiosamine (β-1′′→6, 3′ and 4′) neamines) have been synthesized in a straightforward manner. Peracetylated neomycin azide was used as a common starting material to obtain neobiosamine glycosyl donor and 6, 3′,4′-tri-O-acetyl neamine azide that after simple protecting group manipulation was converted to three different glycosyl acceptors (i.e., 5,6,4′-, 5,3′,4′- and 5,6,3′-tri-O-acetyl neamine azide). Glycosylation between the neobiosamine glycosyl donor and the neamine-derived acceptors gave the protected pseudo-tetrasaccharides, which were converted, via global deprotection (deacetylation and reduction of the azide groups), to the desired site isomers of neomycin. The effect of these aminoglycosides on the RNA and DNA triplex stability was studied by UV-melting profile analysis.

Neamine and 2-deoxystreptamine neomycin derivatives exhibit antinociceptive activity in rat models of phasic, incision and neuropathic pain

Objectives To assess the antinociceptive activity of the neomycin derivatives neamine and 2-deoxystreptamine following intraspinal administration in rats. Methods We used the tail-flick test and measured the threshold to mechanical stimulation in models of incisional and neuropathic pain. Key findings The derivatives produced antinociception in the tail-flick test and reduced mechanical allodynia in models of incisional and neuropathic pain. The approximate ED50 in milligrams (confidence limits in parenthesis) in these tests were 1.35 mg (0.61; 2.95), 0.20 mg (0.14; 0.27) and 0.28 mg (0.12; 0.63) for neamine, and 1.05 mg (0.68; 1.60), 0.78 mg (0.776; 0.783) and 0.79 mg (0.46; 1.34) for 2-deoxystreptamine, respectively. Neamine was more potent than 2-deoxystreptamine in the incisional and neuropathic pain models, but they had similar potency in the tail-flick test. Tetra-azidoneamine, a neamine derivative in which free amino groups are replaced with azido groups, did not change the incisional mechanical allodynia. The reduction of incisional allodynia by neamine and 2-deoxystreptamine was transitorily antagonized by intrathecal administration of calcium chloride. Conclusions The intraspinal administration of neamine and 2-deoxystreptamine is antinociceptive in rats. The presence of amino groups in the structure of these derivatives is fundamental to their antinociceptive effect, which may be due to a calcium antagonist activity.

Synthesis and antibacterial activity of novel neamine derivatives: Preponderant role of the substituent position on the neamine core

A series of neamine derivatives were prepared from the cyclic carbonate and sulfate of 1,3,2′,6′-tetraazido-3′,4′,-di-O- acetylneamine. Ring opening reactions with diversely substituted amines result in the formation of the corresponding carbamates or sulfonic acids with good overall yields. The antibacterial activities of the synthesized products against E. coli (DH5α) and S. aureus (RN4220) were evaluated. With isolated single regioisomers, the preponderant effect of the 5-positions of the carbamate substituent on the neamine core was demonstrated.

An efficient and general route to the synthesis of novel aminoglycosides for RNA binding

An alternative and straightforward method to prepare aminoglycoside dimers and heterodimeric conjugates is reported. The novel type of modification may provide a promising way for the development of new ligands effectively targeting to RNA. Georg Thieme V

Synthesis of neamine-carboline conjugates for RNA binding and their antibacterial activities

Three types of neamine-β-carboline conjugates were synthesized in good yields by the coupling of neamine and β-carboline-3-carboxylic acids using aliphatic diamine as a linker. The binding properties of these conjugates to 16S rRNA and 18S rRNA were evaluated by surface plasmon resonance (SPR), showing that some conjugates had stronger binding affinities than neamine. In vitro antimicrobial activities were also evaluated and the results showed that some synthetic compounds exhibited better antibacterial activities than neamine. The preliminary structure-activity relationship was discussed. The present experimental data demonstrated that synthetic neamine-carboline conjugates might hold the potential as new antibiotics.

Short and efficient synthesis of alkyne-modified amino glycoside building blocks

In the light of recent progress in RNA biology, the need for molecules that bind to RNA and thus may be suited to manipulating RNA-mediated processes is steadily increasing. We present a very short and efficient synthetic route to alkynemodified neamine a

Structure-toxicity relationship of aminoglycosides: Correlation of 2′-amine basicity with acute toxicity in pseudo-disaccharide scaffolds

A new pseudo-disaccharide NB23 with a 3′,4′-methylidene protection was designed and its properties were evaluated in comparison to other two structurally related pseudo-disaccharides. The basicity of the 2′-amine was found to be well correlated to acute toxicity data in mice: the increase in the basicity is associated with the toxicity increase. Based on these data, a new pseudo-trisaccharide NB45 was constructed. NB45 exhibited significant antibacterial activity while at the same time retained low acute toxicity.

A short and scalable route to orthogonally O-protected 2-deoxystreptamine

(Chemical Equation Presented) A seven-step synthesis of orthogonally O-protected 2-deoxy-streptamine has been developed from readily available neomycin, with an overall yield of 28%. Key chemical transformations include a chemoselective glycosidic bond hy

Novel anti bacterial compounds

The invention relates to novel paranmycin compounds that have activity against gram positive and gram negative bacteria, preferably bacteria that are resistant to other antibiotics. Paranmycins are of the general formula