5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C44H49N5O7Si
- MW
- 788.0
- Purity
- 99.02%
5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine is adenosine carrying three protecting groups: a 5'-O-(4,4'-dimethoxytrityl) (DMT) group, a 2'-O-(tert-butyldimethylsilyl) (TBDMS) group, and an N6-benzoyl base-protecting group. CH64110 is identified by CAS 81265-93-2, molecular formula C44H49N5O7Si, molecular weight 788.0, PubChem CID 13871229, and InChIKey DAZIGOPASNJPCJ-GNECSJIWSA-N.
It is an RNA phosphoramidite precursor: the acid-labile 5'-DMT group is removed at the start of each chain-elongation cycle, the 2'-O-TBDMS group protects the ribose 2'-hydroxyl during RNA synthesis, and the N6-benzoyl group masks the adenine exocyclic amine and is removed at final deprotection.
Synonyms
5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine; 5'-O-DMT-2'-O-tert-butyldimethylsilyl-N6-Bz-rA; DMT-2'-TBDMS-rA(Bz)
Identity and specifications
| Catalog No. | CH64110 |
| CAS No. | 81265-93-2 |
| Molecular Formula | C44H49N5O7Si |
| Molecular Weight | 788.0 |
| PubChem CID | 13871229 |
| InChIKey | DAZIGOPASNJPCJ-GNECSJIWSA-N |
| Purity | 99.02% |
Storage conditions
2-8 C
Technical attributes
- Nucleobase
- Adenine
- 5'-O protection
- DMT (dimethoxytrityl)
- 2'-O protection
- TBDMS (tert-butyldimethylsilyl)
- Base protection
- N6-Benzoyl
- Packaging
- 5 mg; 250 mg; Custom packaging on request
- Water content
- <=1.0%
- Physical form
- white to off-white powder
- Stability
- 3 years at -20 C
Application context
- 5'-DMT 5'-OH protection: the acid-labile 4,4'-dimethoxytrityl group protects the 5'-hydroxyl and is removed at the start of each RNA chain-elongation cycle.
- 2'-O-TBDMS 2'-OH protection: the tert-butyldimethylsilyl group protects the ribose 2'-hydroxyl during solid-phase RNA synthesis.
- N6-benzoyl base protection: the benzoyl group masks the adenine exocyclic amine during synthesis and is removed at final deprotection.
Related technical resources
Oligonucleotide Modification
Sugar, base, backbone, terminal, and conjugation modifications for ASO, siRNA, guide RNA, aptamer, and research or labeling oligo projects.
Oligonucleotide Synthesis
Support for modified monomers, supports, sulfurizing reagents, cap analogs, and related oligo synthesis inputs.
Public references
- Sustainability Challenges and Opportunities in Oligonucleotide Manufacturing
Journal of Organic Chemistry, 2021
Product-family technical context
- Solid-phase supports for oligonucleotide synthesis
Current Protocols in Nucleic Acid Chemistry, 2013
Product-family technical context
- Deoxynucleoside phosphoramidites—A new class of key intermediates for deoxypolynucleotide synthesis
Tetrahedron Letters, 1981
Product-family technical context
- Synthesis of deoxyoligonucleotides on a polymer support
Journal of the American Chemical Society, 1981
Product-family technical context
- PubChem Compound 13871229
PubChem · CID 13871229
Frequently Asked Questions
What do the three protecting groups on this adenosine do?
The 5'-O-DMT group is an acid-labile 5'-hydroxyl protection removed at the start of each RNA chain-elongation cycle; the 2'-O-TBDMS group protects the ribose 2'-hydroxyl during solid-phase RNA synthesis; and the N6-benzoyl group protects the adenine exocyclic amine, removed at final deprotection.
How does it differ from 5'-O-DMT-N6-benzoyl-2'-deoxyadenosine?
This is the ribonucleoside form with a 2'-hydroxyl protected as a 2'-O-TBDMS ether (for RNA synthesis), whereas the deoxy version has no 2'-OH. The 2'-deoxy form is cataloged separately.
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