13039-67-3

Usage

Uses

Used in Pharmaceutical Applications:
(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol is used as an active pharmaceutical ingredient for its potential biological activities, which may include therapeutic effects in various medical conditions.
Used in Chemical Applications:
In the chemical industry, (2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol is used as an intermediate in the synthesis of other complex organic compounds, taking advantage of its unique structural features and reactivity.
Used in Research:
(2S,3S,4S)-2-(hydroxymethyl)-5-methoxyoxolane-3,4-diol is utilized as a subject of study in organic and biochemistry research to explore its properties, potential reactions, and applications in creating new compounds and understanding biological processes.

Upstream product

• 67-56-1 methanol 
• 1114-34-7 D-lyxose 
• 532-20-7 D-lyxose 
• 50-69-1 D-ribose 
• 2280-44-6 D-Glucose 
• 582-52-5 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 37077-81-9 1,2-isopropylidene-α-D-ribofuranose 
• 2847-00-9 1,2:5,6-di-O-isopropylidene-α-D-hexofuran-3-ulose 
• 2595-05-3 Diacetone D-glucose 
• 4495-04-9 1,2-O-isopropylidene-α-D-allofuranose 
• 63846-98-0 1,2-O-(1-Methylethylidene)-α-D-ribo-pentodialdo-1,4-furanose 
• 36468-53-8 β-D-ribofuranose 
• 532-20-7 D-xylofuranose 
• 58-86-6 D-xylose 

Downstream Products

• 77841-39-5 methyl 2,3,5-tri-O-acetyl-D-lyxofuranoside 
• 64363-77-5 methyl 2,3,5-tri-O-benzyl-D-ribofuranoside 
• 50908-04-8 (-)-Methyl-5-O-trityl-β-D-ribofuranosid 
• 67689-93-4 methyl 5-O-trityl-α-D-ribofuranoside 
• 52783-53-6 methyl 2,3,3'-tri-O-benzoyl-β-D-apiofuranoside 
• 52783-87-6 methyl 2,3,5-tri-O-benzoyl-α-D-ribofuranoside 
• 69350-76-1 methyl 2,3,5-tri-O-benzoyl-αβ-D-ribofuranoside 
• 108008-65-7 methyl 2,3,5-tri-O-(4-chlorobenzyl)-β-D-ribofuranoside 
• 83376-69-6 methyl 2,3-di-O-methyl-D-riboside 
• 83376-70-9 methyl 2,5-di-O-methyl-D-riboside 
• 83376-68-5 methyl 3,5-di-O-methyl-D-riboside 
• 2296-41-5 methyl 2,3,5-tri-O-methyl-D-ribofuranoside 
• 303041-42-1 methyl 2,3,5-tri-O-[3-(trifluoromethyl)benzoyl]-D-ribofuranoside 
• 4099-85-8 methyl 2,3-O-isopropylidene-D-ribofuranoside 

Relevant academic research and scientific papers

Transformation of Sugars into Chiral Polyols over a Heterogeneous Catalyst

Transformation of sugars, while maintaining the intrinsic stereochemical structure, is desirable. However, such a transformation requires multistep synthesis with protection and deprotection of the OH groups. Herein, a new method for selective transformation of sugar derivatives into chiral building blocks and a diol synthon, with retention of the intrinsic configuration (stereo- and regioselectively), is demonstrated. The method is based on the selective recognition of cis-vicinal OH groups in sugars and leads to the one-pot removal of the cis-vicinal OH groups, without protection of OH groups (except the OH group of the hemiacetal group), over a heterogeneous CeO2-supported ReOx and Pd (ReOx-Pd/CeO2) catalyst by using H2 as a reducing agent.

MODIFIED OLIGOMERIC COMPOUNDS AND USES THEREOF

The present disclosure provides oligomeric compounds comprising a modified oligonucleotide having at least one stereo-non-standard nucleoside. An oligomeric compound comprising a modified oligonucleotide consisting of 12-30 linked nucleosides, wherein at least one nucleoside of the modified oligonucleotide is a stereo-non-standard nucleoside; and wherein the oligomeric compound is selected from among an RNAi compound, a modified CRISPR compound, and an artificial mRNA compound.

Novel saccharide bio-based cyclic phosphorus/phosphonate as well as preparation method and application thereof

The invention discloses novel saccharide bio-based cyclic phosphorus/phosphonate as well as a preparation method and application thereof, and belongs to the field of compounds. The cyclic phosphorus/phosphonate is prepared by the following steps: reacting D-xylose with acetyl chloride to obtain an intermediate product, and then reacting with dichlorophosphate or phosphonic dichloride under the action of an acid-binding agent to obtain a target product. The preparation method is high in yield, simple in process, low in raw material cost and small in environmental pollution, and the prepared cyclic phosphorus/phosphonate flame retardant is outstanding in flame retardance and easy to industrialize.

Stereoselective Synthesis of Ribofuranoid exo-Glycals by One-Pot Julia Olefination Using Ribofuranosyl Sulfones

One-pot Julia olefination using ribofuranosyl sulfones is described. The α-anomers of the ribofuranosyl sulfones were synthesized with complete α-selectivity via the glycosylation of heteroarylthiols using ribofuranosyl iodides as glycosyl donors and the subsequent oxidation of the resulting heteroaryl 1-thioribofuranosides with magnesium monoperphthalate (MMPP). The Julia olefination of the α-ribofuranosyl sulfones with aldehydes proceeded smoothly in one pot to afford the thermodynamically less stable (E)-exo-glycals with modest-to-excellent stereoselectivity (up to E/Z = 94:6) under the optimized conditions. The E selectivity was especially high for aromatic aldehydes. In contrast, the (Z)-exo-glycal was obtained as the main product with low stereoselectivity when the corresponding β-ribofuranosyl sulfone was used (E/Z = 41:59). The remarkable impact of the anomeric configuration of the ribofuranosyl sulfones on the stereoselectivity of the Julia olefination has been rationalized using density functional theory (DFT) calculations. The protected ribose moiety of the resulting exo-glycals induced completely α-selective cyclopropanation on the exocyclic carbon-carbon double bond via the Simmons-Smith-Furukawa reaction. The 2-cyanoethyl group was found to be useful for the protection of the exo-glycals, as it could be removed without affecting the exocyclic C=C bond.

BIOMARKER PANEL TARGETED TO DISEASES DUE TO MULTIFACTORIAL ONTOLOGY OF GLYCOCALYX DISRUPTION

The present disclosure provides biomarkers useful as companion diagnostics for detecting glycocalyx-based disease that is amenable to treatment using compounds designed for improving the condition of the glycocalyx and/or reducing inflammation and/or oxidative damage, as well as related compositions, kits, and methods.

Glycosides and Glycoconjugates of the Diterpenoid Isosteviol with a 1,2,3-Triazolyl Moiety: Synthesis and Cytotoxicity Evaluation

Several glycoconjugates of the diterpenoid isosteviol (16-oxo-ent-beyeran-19-oic acid) with a 1,2,3-triazolyl moiety were synthesized, and their cytotoxicity was evaluated against some human cancer and normal cell lines. Most of the synthesized compounds demonstrated weak inhibitory activities against the M-HeLa and MCF-7 human cancer cell lines. Three lead compounds, 54, 56 and 57, exhibited high selective cytotoxic activity against M-HeLa cells (IC50 = 1.7-1.9 μM) that corresponded to the activity of the anticancer drug doxorubicin (IC50 = 3.0 μM). Moreover, the lead compounds were not cytotoxic with respect to a Chang liver human normal cell line (IC50 > 100 μM), whereas doxorubicin was cytotoxic to this cell line (IC50 = 3.0 μM). It was found that cytotoxic activity of the lead compounds is due to induction of apoptosis proceeding along the mitochondrial pathway. The present findings suggest that 1,2,3-triazolyl-ring-containing glycoconjugates of isosteviol are a promising scaffold for the design of novel anticancer agents.

ANTIVIRAL NUCLEOSIDES AND DERIVATIVES THEREOF

Disclosed herein are nucleoside compounds and derivatives thereof, pharmaceutical compositions containing same, and their methods of synthesis. The compounds are useful in treating orthomyxovirus infections, such as influenza infections.

Synthesis of remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone

The invention relates to synthesis of a remdesivir key intermediate 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone. The invention discloses a synthesis method of 2, 3, 5-tribenzyloxy-D-ribotide-1, 4-lactone, and belongs to the field of organic synthesis. The method includes: taking D-ribose as an initial raw material, in methanol, using concentrated sulfuric acid as a catalyst, synthesizing a methoxy compound 2, then fully stirring the substances in a saturated sodium hydroxide solution, adding tetrahydrofuran and n-butylammonium hydrogen sulfate, and then adding benzyl bromide to synthesize a compound 3, dissolving the compound 3 in tetrahydrofuran and then performing catalysis with concentrated sulfuric acid, and performing reflux stirring overnight treatment to obtain a compound 4, dissolving the compound 4 into dichloromethane and water, adding sodium bicarbonate and TEMPO, slowly adding sodium hypochlorite at 0DEG C, raising the temperature to room temperature, and conducting stirring overnight treatment to obtain a compound 5. The method has the characteristics of easily available raw materials and low production cost, each process step is simple and easy to treat, the yield ofthe whole route reaches 43% or above, industrial production is easy to realize, and a basis is provided for industrialization of remdesivir and subsequent derivatives thereof.

Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof

The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.

2-Hydroxyimino-6-aza-pyrimidine nucleosides: Synthesis, DFT calculations, and antiviral evaluations

The global public health concerns and economic impact caused by emerging outbreaks of RNA viruses call for the search for new direct acting antiviral agents. Herein, we describe the synthesis, DFT calculations, and antiviral evaluation of a series of novel 2-hydroxyimino-6-aza-pyrimidine ribonucleosides. DFT//B3LYP/6-311+G?? calculations of the tautomeric distributions of the 2-hydroxyimino nucleosides 7, 8, and 9 in aqueous environments indicate a predominance of the canonical 2-(E)-hydroxyimino structure, where the hydroxyl group points away from the sugar moiety. The conformer distributions of the latter geometrical isomers of 7, 8, and 9 support the formation of five membered rings via hydrogen bonding between the (E)-C2N-O-H moiety and N3-H of 7 and 8 and between (E)-C2N-O-H and N3 of 9, creating purine shaped nucleosides with the glycosidic linkage at the pyrimidine ring. The newly synthesized nucleosides were screened against an RNA viral panel, of which moderate antiviral activity was observed against Zika virus (ZIKV) and human respiratory syncytial virus (HRSV). 6-Aza-2-hydroxyimino-5-methyluridine derivative 18 showed activity against ZIKV (EC50 3.2 μM), while its peracetylated derivative 19 showed activity against HRSV (EC50 5.2 μM). The corresponding 4-thiono-2-hydroxyimino derivative 8 showed activity against HRSV (EC50 6.1 μM) and against ZIKA (EC50 2.4 μM). This study shows that the 6-aza-2-hydroxyimino-5-methyluracil derived nucleosides can be further optimized to provide potent antiviral agents. This journal is