Oligonucleotide Synthesis, RNA Raw Materials & Modification

5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine

Oligonucleotide Synthesis, RNA Raw Materials & Modification

产品编号CH64110CAS号81265-93-2纯度99.02%

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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: C44H49N5O7Si
分子量: 788.0
纯度: 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.

同义词

5'-O-DMT-2'-O-TBDMS-N6-benzoyladenosine; 5'-O-DMT-2'-O-tert-butyldimethylsilyl-N6-Bz-rA; DMT-2'-TBDMS-rA(Bz)

身份与规格

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%

储存条件

2-8 C

技术属性

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

应用背景

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.

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 13871229
PubChem · CID 13871229

常见问题

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.