2'-O-TBDMS-A (Bz) 3'-PS Thiophosphoramidite
Oligonucleotide Synthesis, RNA Raw Materials & Modification
Product summary
Quick view
- Product family
- Oligonucleotide Synthesis, RNA Raw Materials & Modification
- MF
- C57H65N6O8PS2Si
- MW
- 1085.4
- Purity
- >=95%
2'-O-TBDMS-A (Bz) 3'-PS Thiophosphoramidite is a phosphorothioate-linkage RNA building block: a 5'-O-(4,4'-dimethoxytrityl)-N6-benzoyl-2'-O-(tert-butyldimethylsilyl)adenosine 3'-thiophosphoramidite. It is identified by CAS 1374755-65-3, molecular formula C57H65N6O8PS2Si, molecular weight 1085.4, PubChem CID 102308172, and InChIKey ALJIYXCITZABFP-WOMFGPHHSA-N.
As a thiophosphoramidite it provides the sulfur-bearing phosphorus chemistry used for phosphorothioate (PS) linkage synthesis. The cited phosphorothioate literature discusses PS linkages in relation to nuclease resistance. The 2'-O-TBDMS group is the silyl protecting group for the 2'-hydroxyl in RNA synthesis; the 5'-DMT is removed each cycle and the N6-benzoyl base-protecting group is removed during final deprotection.
Synonyms
2-OTBS A(Bz) ThioPhosphamidite; 5'-O-DMT-N6-Bz-2'-O-TBDMS-adenosine 3'-thiophosphoramidite
Identity and specifications
| Catalog No. | CH65080 |
| CAS No. | 1374755-65-3 |
| Molecular Formula | C57H65N6O8PS2Si |
| Molecular Weight | 1085.4 |
| PubChem CID | 102308172 |
| InChIKey | ALJIYXCITZABFP-WOMFGPHHSA-N |
| Purity | >=95% |
Storage conditions
-20 C
Technical attributes
- Monomer class
- RNA thiophosphoramidite
- Nucleobase
- Adenine
- 2'-O protection
- TBDMS
- Linkage role
- Phosphorothioate linkage precursor
- Packaging
- 1 g; Custom packaging on request
Application context
- Phosphorothioate (PS) linkage: the thiophosphoramidite provides sulfur-bearing phosphorus chemistry for PS linkage synthesis.
- PS literature context: the cited phosphorothioate literature discusses PS linkages in relation to nuclease resistance.
- 2'-O-TBDMS RNA protection: the tert-butyldimethylsilyl group protects the 2'-hydroxyl during solid-phase RNA synthesis.
- Protection scheme: the 5'-DMT is removed each cycle and the N6-benzoyl base-protecting group is removed during 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 102308172
PubChem · CID 102308172
Frequently Asked Questions
How does this differ from the standard 2'-O-TBDMS-rA(Bz) amidite?
It is a thiophosphoramidite rather than a standard phosphoramidite: the phosphorus chemistry is used for phosphorothioate (PS) linkage synthesis, whereas the standard amidite is used for phosphodiester linkage synthesis. Both carry 5'-DMT, 2'-O-TBDMS, and N6-benzoyl protection.
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