5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine

Name: 5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine
Brand: ChemScene
Availability: InStock
Rating: 5 (1 reviews)

CAS No. 103285-22-9
Cat. No. CS-0061965
Purity≥95%
MDL No.MFCD00274123

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Type	HazMat Fee
Excepted Quantity	$0.00
FedEx Limited Quantities Ground	$0.00
Hazmat Ground shipping	$50.00+
Inaccessible (Haz class 6.1 or 9), Domestic	$68.00+
Accessible (Haz class 3, 4, 5 or 8), Domestic	$158.00+
Inaccessible (Haz class 6.1 or 9), International	$108.00+
Accessible (Haz class 3, 4, 5 or 8), International	$238.00+

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5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine|CS-0061965

Structure of 103285-22-9

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General Information

CAS No. 103285-22-9
Cat. No. CS-0061965
Purity ≥95%
MDL No. MFCD00274123
Storage 4°C
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₃₁H₃₂N₂O₈
Molecular Weight 560.59
Synonym(s) None
SMILES O[C@H]1[C@@H](OC)[C@H](N2C(NC(C=C2)=O)=O)O[C@@H]1COC(C3=CC=C(OC)C=C3)(C4=CC=CC=C4)C5=CC=C(OC)C=C5

Description

5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine delivers a protected nucleoside scaffold for automated oligonucleotide synthesis. The dimethoxytrityl group enables efficient 5’-end labeling and chain elongation, while the 2’-O-methyl modification enhances nuclease resistance and conformational stability in synthetic RNA analogs. This derivative supports high-fidelity incorporation under standard phosphoramidite coupling conditions.

Application

5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine serves as a key building block in the synthesis of modified oligonucleotides, enabling efficient 3’→5’ phosphodiester linkage formation. The 4,4’-dimethoxytrityl group provides robust protection at the 5’-hydroxyl, facilitating controlled chain elongation and ease of purification via trityl cation monitoring. The 2’-O-methyl modification enhances nuclease resistance and improves binding affinity, making this derivative ideal for antisense and RNAi applications requiring enhanced stability and target specificity.

Synthesis

Route1
- 109-88-6
- 173170-12-2
- ~65%
- In-stock
  
  103285-22-9
References
- Buettner, Lea; Seikowski, Jan; Wawrzyniak, Katarzyna; Ochmann, Anne; Hoebartner, Claudia Bioorganic and Medicinal Chemistry, 2013 , vol. 21, # 20 p. 6171 - 6180
Route2
- In-stock
  
  40615-36-9
- ~99%
- In-stock
  
  103285-22-9
References
- ISIS Pharmaceuticals, Inc. Patent: US5914396 A1, 1999 ;
Route3
- In-stock
  
  40615-36-9
- In-stock
  
  2140-76-3
- ~90%
- In-stock
  
  103285-22-9
References
- Barbeyron, Renaud; Wengel, Jesper; Vasseur, Jean-Jacques; Smietana, Michael Monatshefte fur Chemie, 2013 , vol. 144, # 4 p. 495 - 500

Safety Information

Download SDS

GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H315-H319-H335
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362+P364-P403+P233-P405-P501

Quality Control

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Computational Chemistry Data

TPSA 121.24
LogP 2.8358
H_Acceptors 9
H_Donors 2
Rotatable_Bonds 10

Other Classifications

Life Science Nucleosides & Nucleotides 2'-O-MOE-modified Nucleoside

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Building Blocks Skeleton Aromatic ring compounds Benzene compounds

Chemical Biology Nucleic Acid Chemistry Methylated Nucleosides

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleobases and their Analogs

Biochemistry Biochemicals and Reagents Nucleosides, Nucleotides, Oligonucleotides Nucleoside Analogs

Key Words

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5’-O-(4,4’-Dimethoxytrityl)-2’-O-methyluridine

CAS No. 103285-22-9

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