Lot numbers can be found on the outside label of a product:
TK-112690
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CAS No. 22423-26-3
- Cat. No. CS-W008491
- Purity≥95%
- MDL No.MFCD00233555
*For research and further manufacturing use only, not for direct human use.
Structure of 22423-26-3
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General Information
- CAS No. 22423-26-3
- Cat. No. CS-W008491
- Purity ≥95%
- MDL No. MFCD00233555
- Storage 4°C
- Shipping Room temperature in continental US; may vary elsewhere.
- Molecular Formula C₁₀H₁₂N₂O₅
- Molecular Weight 240.21
- Synonym(s) None
- SMILES CC(C1=O)=CN(C2=N1)[C@@]3([H])[C@](O2)([H])[C@@](O)([H])[C@@](O3)([H])CO
Description
2,2'-Anhydro-5-methyluridine features a rigidified furanose ring system that enhances conformational stability in nucleoside analogs. This structural constraint improves resistance to enzymatic degradation while maintaining favorable binding affinity for RNA polymerases. The 5-methyl group contributes to enhanced hydrophobic interactions in duplex contexts, making this derivative valuable for probing nucleic acid dynamics and designing stable antisense oligonucleotides.
Application
2,2'-Anhydro-5-methyluridine serves as a valuable building block in nucleoside synthesis, offering a rigidified furanose scaffold that facilitates stereoselective glycosylation reactions. Its anhydro bridge enhances conformational stability and improves resistance to hydrolysis, enabling reliable use in automated oligonucleotide assembly and the construction of modified RNA analogs. The 5-methyl substitution provides enhanced metabolic stability and improved binding affinity in therapeutic applications.
Synthesis
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Route1
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In-stock
1463-10-1 - ~90%
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In-stock
22423-26-3
References
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Brown, Tom; El-Sagheer, Afaf Helmy Patent: US2013/231473 A1, 2013 ; Location in patent: Paragraph 0158 ;
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References
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Isis Pharmaceuticals Inc. Patent: US2004/77085 A1, 2004 ; Location in patent: Page/Page column 16 ;
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Route3
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26879-47-0 - ~75%
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In-stock
22423-26-3
References
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MARINA BIOTECH INC.; MATRAY, Tracy J.; MACIAGIEWICZ, Iwona M.; HOUSTON, Michael E., Jr. Patent: WO2013/36868 A1, 2013 ; Location in patent: Page/Page column 30; 31 ;
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Safety Information
Download SDS|
GHS Pictogram :
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GHS No : GHS07
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Signal Word : Warning
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UN#: N/A
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Class : N/A
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Packing Group : N/A
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Hazard Statements : H302-H315-H319-H335
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Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501
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Quality Control
Computational Chemistry Data
- TPSA 93.81
- LogP -1.43668
- H_Acceptors 7
- H_Donors 2
- Rotatable_Bonds 1
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Key Words
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