22423-26-3

Basic information

• Product Name: 2,2'-Anhydro-5-methyluridine
• Synonyms: 2,2'-anhydro-1-beta-arabinofuranosylthymine;2,2'-ANHYDRO-(1-BETA-D-ARABINOFURANOSYL)THYMINE;2,2'-Anhydro-11-beta-D-arabinofuranosylthymine;2,2'-ANHYDRO-(1-E-D-ARABINOFURANOSYL)-5-METHYLURACIL;2,2'-ANHYDRO-5-METHYLURIDINE;2,2'-ANHYDROTHYMIDINE;(2r-(2alpha,3beta,3abeta,9abeta))-2,3,3a,9a-tetrahydro-3-hydroxy-2-(hydroxymethyl)-7-methyl-6h-furo(2',3':4,5)oxazolo(3,2-a)pyrimidin-6-one;6H-FURO[2',3':4,5]OXAZOLO[3,2-A]PYRIMIDIN-6-ONE,2,3,3A,9A-TETRAHYDRO-3-HYDROXY-2-(HYDROXYMETHYL)-7-METHYL-, (2R,3R,3AS, 9AR)-
• CAS NO: 22423-26-3
• Molecular Formula: C₁₀H₁₂N₂O₅
• Molecular Weight: 240.21
• EINECS: 2017-001-1
• Mol File: 22423-26-3.mol

Chemical Properties

• Melting Point: 217.0 to 221.0 °C
• Boiling Point: 452.0±55.0 °C at 760 mmHg
• Flash Point: 227.2±31.5 °C
• Appearance: Colourless solid
• Density: 1.9±0.1 g/cm³
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 12.56±0.60(Predicted)
• Water Solubility: Soluble in water
• CAS DataBase Reference: 2,2'-Anhydro-5-methyluridine(CAS DataBase Reference)
• NIST Chemistry Reference: 2,2'-Anhydro-5-methyluridine(22423-26-3)
• EPA Substance Registry System: 2,2'-Anhydro-5-methyluridine(22423-26-3)

Safety Data

• Hazardous Substances Data: 22423-26-3(Hazardous Substances Data)

Usage

Chemical Properties

Colourless solid

Upstream product

• 1463-10-1 5-Methyluridine 
• 68-12-2 N,N-dimethyl-formamide 
• 52486-19-8 1-(β-D-xylofuranosyl)-thymine 
• 512781-08-7 1-(3,5-O-sulfinyl-β-D-xylofuranosyl)thymine 
• 3180-76-5 2',3',5'-tri-O-benzoyluridine 
• 65-71-4 thymin 
• 14215-97-5 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 
• 532-20-7 D-xylofuranose 
• 42927-45-7 3,5,6-tri-O-acetyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 20031-21-4 1,2-O-isopropylidene-α-D-xylose 
• 20881-04-3 1,2:3,5-di-O-isopropylidene-D-xylofuranose 
• 25545-03-3 β-D-arabinofuranose 
• 27963-98-0 2-amino-β-D-arabinofurano[1',2':4,5]-oxazoline 
• 102-09-0 bis(phenyl) carbonate 

Downstream Products

• 52259-53-7 (3aS)-3c-hydroxy-2t-hydroxymethyl-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-8-one 
• 154534-68-6 2'-deoxy-2'-methylthio-5-methyluridine 
• 95585-76-5 2'-bromothymidine 
• 605-23-2 thymine arabinoside 
• 39687-10-0 (3aS)-3c-acetoxy-2t-acetoxymethyl-7-methyl-(3ar,9ac)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 127840-90-8 3-(3,5-di-O-monomethoxytrityl-β-D-arabinofuranosyl)thymine 
• 127941-51-9 2,2'-Anhydro-1-<3',5'-bis-O-(tert-butyldimethylsilyl)-β-D-arabinofuranosyl>thymine 
• 171763-19-2 5'-O-tert-butyldiphenylsilyl-O²-2'-anhydro-5-methyluridine 
• 242147-77-9 2'-O-phthalimidoethyl-5-methyluridine 
• 351523-06-3 (2R,3R,3aS,9aR)-7-Methyl-3-(tetrahydro-pyran-2-yloxy)-2-(tetrahydro-pyran-2-yloxymethyl)-2,3,3a,9a-tetrahydro-furo[2',3':4,5]oxazolo[3,2-a]pyrimidin-6-one 
• 54898-34-9 2'-chlorothymidine 
• 97748-75-9 1-(2'-azido-2'-deoxy-β-β-D-ribofuranosyl)thymine 
• 10212-31-4 β-D-arabinofuranosyl-5-methylisocytosine 
• 253145-84-5 2'-O-[2-(2-(N,N-dimethylamino)ethoxy)ethyl]-5-methyluridine 

Relevant articles and documents

Facile Synthesis of 5-Substituted Arabinofuranosyluracil Derivatives

Arabinoaminooxazoline reacted readily with α-(bromomethyl)acrylate derivatives to afford the corresponding adduct.Potassium tert-butoxide- or sodium methoxide-catalyzed cyclization of the adduct gave 5-substituted 2,2'-anhydroarabinofuranosyluracil derivatives.

Method for preparing β-thymidine

The invention relates to a preparation method of beta-thymidine, and specifically discloses a method of preparing beta-thymidine from the formula II compound. The method comprises following steps: subjecting the compound represented as the formula II to carry out dehalogenation reactions, in a hydrogen atmosphere, in the presence of a catalyst, and in a buffer system with a pH value of 6.5 to 8.0, so as to obtain beta-thymidine represented as the formula I, wherein X represents Cl or Br. The dehalogenation reactions are carried out under atmospheric pressure, and the preparation method has the advantages of environment-friendliness, economy, high product yield, good product purity, and suitability for industrial production.

METHODS FOR THE PREVENTION AND TREATMENT OF MAJOR ADVERSE CARDIOVASCULAR EVENTS USING COMPOUNDS THAT MODULATE APOLIPOPROTEIN B

Provided herein, for example, are methods generally relating to preventing, treating and/or managing a major adverse cardiovascular event in a subject with a disease or condition at risk for a major adverse cardiovascular event, e.g., familial hypercholesterolemia. Also provided herein are methods relating to administering to the patient a therapeutically effective amount of an antisense oligonucleotide having a nucleobase SEQ ID NO: 247 (e.g., mipomersen).

A new straightforward synthesis of 2′,3′-didehydro-2′,3′-dideoxy-2′-(2″-(trimethylsilyl)ethylthio)thymidine, key intermediate for the synthesis of 2′-substituted thionucleosides

We describe herein a straightforward and efficient preparation of 2′,3′-dideoxy-2′-(2″-(trimethylsilyl)ethylthio)thymidine, which allows the preparation of diverse potentially antiviral and/or anticancer nucleosides (disulfides, thiols, sulfides, thiocyanates).

Cu(I)-catalyzed efficient synthesis of 2'-triazolo-nucleoside conjugates

A small library of thirty-two 2'-triazolyl uridine and 2'-triazolyl-5-methyluridine has been synthesized by Cu(I)-catalyzed condensation of 2'-azido-2'-deoxyuridine and 2'-azido-2'-deoxy-5-methyluridine with different alkynes and aryl propargyl ethers in almost quantitative yields. Triazolo-nucleoside conjugates, which can be evaluated for different biological activity for suitable drug development, were unambiguously identified on the basis of 1H NMR, 13C NMR, IR, and HRMS data analysis. These compounds have been synthesized for the first time and have not been reported in the literature earlier.

EFFECTS OF APOLIPOPROTEIN B INHIBITION ON GENE EXPRESSION PROFILES IN ANIMALS

Antisense compounds, compositions and methods are provided for modulating the expression of apolipoprotein B. The compositions comprise antisense compounds, particularly antisense oligonucleotides, targeted to nucleic acids encoding apolipoprotein B. Methods of using these compounds for modulation of apolipoprotein B expression and for treatment of diseases associated with expression of apolipoprotein B are provided. Methods are provided for modulating the expression of genes involved in lipid metabolism, useful in the treatment of conditions associated with cardiovascular risk. Antisense oligonucleotides targeted to apolipoprotein B reduce the level of apolipoprotein B mRNA, lower serum cholesterol and shift liver gene expression profiles from those of an obese animal towards those of a lean animal. Further provided are methods for improving the cardiovascular risk of a subject through antisense inhibition of apolipoprotein B. Also provided are methods for employing antisense oligonucleotides targeted to apolipoprotein B to modulate a cellular pathway or metabolic process.

OLIGONUCLEOTIDE LIGATION

A method for joining oligonucleotides. The method includes joining together one or more oligonucleotides by reacting an alkyne group lined to an oligonucleotide with an azide group linked to an oligonucleotide to form a triazole linkage. The alkyne group is a strained alkyne group. The method can include ligating together ends of one or more oligonucleotides or cross-linking strands of an oligonucleotide duplex. The methods described allow oligonucleotide strands to be ligated together without the need for a ligase enzyme.

SYNTHESIS AND USES OF NUCLEIC ACID COMPOUNDS WITH CONFORMATIONALLY RESTRICTED MONOMERS

Synthesis and uses of conformationally restricted nucleomonomers (CRN) to prepare nucleic acid compounds. Methods for preparing nucleomonomers for nucleic acid compounds in high yields and in multi-gram scale for therapeutic modalities useful for treating or preventing diseases or disorders by up- or down-regulating the expression of genes and other nucleic acid based regulatory systems in a cell.

NUCLEOSIDE BASED PROLIFERATION IMAGING MARKERS

Disclosed herein are novel radiolabeled nucleosides and methods for detecting cellular proliferation in a mammal, the method comprising administrating an effective amount of a radiolabeled nucleoside; the method comprising: a) administering to the mammal a diagnostically effective amount of the nucleoside to the mammal; b) allowing the nucleoside to distribute into the effective tissue; and c) imaging the tissue, wherein an increase in binding of the compound to tissue compared to a normal control level of binding indicates that the mammal is suffering from a disease involving cellular proliferation.

New telluride-mediated elimination for novel synthesis of 2′,3′-didehydro-2′,3′-dideoxynucleosides

(Chemical Equation Presented) Several 2′,3′-dideoxynucleosides (ddNs) and 2′,3′-didehydro-2′,3′-dideoxynucleosides (d4Ns) are FDA-approved anti-HIV drugs. Via conveniently synthesized 2,2′-anhydronucleosides, we have developed a novel synthesis of d4Ns by discovering and applying a new telluride-mediated elimination reaction. Our experiment results show that after substitution of 2,2′-anhydronucleosides with a telluride monoanion, a telluride intermediate is formed, and its elimination leads to formation of the olefin products (d4Ns). Our mechanistic study indicates that this telluride-assisted reaction consists of two steps: substitution (or addition) and elimination. By using dimethyl ditelluride (0.1 equiv) as the reagent, d4Ns can be synthesized with yields up to 90% via this telluride-mediated elimination. Our novel strategy has great potential to simplify synthesis of these drugs and to further reduce cost of AIDS treatment and will also facilitate development of novel d4N and ddN analogues.