Oligonucleotide Synthesis, RNA Raw Materials & Modification

2'-O-TBDMS-Adenosine (Bz) CE Phosphoramidite

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH65010CAS号104992-55-4纯度100.0% (NMR)

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产品概述

快速信息

产品系列: Oligonucleotide Synthesis, RNA Raw Materials & Modification
分子式: C53H66N7O8PSi
分子量: 988.2
纯度: 100.0% (NMR)

2'-O-TBDMS-Adenosine (Bz) CE Phosphoramidite is the fully protected adenosine building block for RNA synthesis: 5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)-N6-benzoyladenosine bearing a 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite group. CH65010 is identified by CAS 104992-55-4, molecular formula C53H66N7O8PSi, molecular weight 988.2, PubChem CID 11355126, and InChIKey FFXHNCNNHASXCT-RFMFGJHUSA-N.

Nucleoside phosphoramidites are the coupling monomers used in automated solid-phase RNA synthesis: the 3'-phosphoramidite is the reactive group that couples to the growing chain, the acid-labile 5'-DMT is removed at the start of each cycle, the 2'-O-TBDMS protects the ribose 2'-hydroxyl, and the N6-benzoyl base group is removed at final deprotection.

同义词

DMT-2'-O-TBDMS-rA(Bz) phosphoramidite; 5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine 3'-CE phosphoramidite

身份与规格

Catalog No.	CH65010
CAS No.	104992-55-4
Molecular Formula	C53H66N7O8PSi
Molecular Weight	988.2
PubChem CID	11355126
InChIKey	FFXHNCNNHASXCT-RFMFGJHUSA-N
Purity	100.0% (NMR)

储存条件

-20 C, dry inert atmosphere

技术属性

Monomer class: RNA CE phosphoramidite
Nucleobase: Adenine
2'-O protection: TBDMS (tert-butyldimethylsilyl)
Base protection: N6-Benzoyl
Grade: N (Normal)
Packaging: 250 mg; 500 mg; 1 g; 2 g; 5 g; 10 g; 25 g; 50 g; 100 g; 200 g; Custom packaging on request
Water content: <=0.3%
Physical form: white to faint yellow powder
Stability: Manufactured 2024-01-17; retest 2027-07-20; expiry 2028-01-16

应用背景

RNA coupling monomer: the 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite is the reactive group that couples to the growing oligonucleotide chain in automated solid-phase RNA synthesis.
5'-DMT + 2'-O-TBDMS protection: the acid-labile 5'-DMT is removed each cycle, while the 2'-O-TBDMS group protects the ribose 2'-hydroxyl during synthesis.
N6-benzoyl base protection: the benzoyl group masks the adenine exocyclic amine during synthesis and is removed at final deprotection.

公开来源

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 化合物 11355126
PubChem · CID 11355126

常见问题

What are the four functional groups on this RNA amidite?

A 3'-O-(2-cyanoethyl N,N-diisopropyl)phosphoramidite (the reactive coupling group), an acid-labile 5'-O-DMT group (removed each cycle), a 2'-O-TBDMS group (protects the ribose 2'-hydroxyl), and an N6-benzoyl base protection (removed at final deprotection).

How does it relate to 5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine?

It is the phosphoramidite of that nucleoside: the 3'-hydroxyl has been converted to a 2-cyanoethyl N,N-diisopropyl phosphoramidite. The precursor is cataloged separately.