N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 104992-55-4
• Molecular Formula: C₅₃H₆₆N₇O₈PSi
• Molecular Weight: 988.208
• Hs Code.: 29349990
• Mol file: 104992-55-4.mol

Synonyms:5'-O-DMT-2'-TBDMS-rA(N-Bz)-3'-CEDPA

Chemical Property of N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

• PKA: 7.87±0.43(Predicted)
• PSA: 177.93000
• LogP: 11.12650
• Storage Temp.: ?20°C

Purity/Quality:

98% ^*data from raw suppliers

DMT-2′O-TBDMS-rA(bz) Phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite can be used as Organic synthesis intermediates and pharmaceutical intermediates are mainly used in laboratory research and development processes and chemical production processes. DMT-2''O-TBDMS-rA(bz) Phosphoramidite is a 2''-O-Protected ribonucleoside phosphoramidite used as a key raw material for the automated solid-supported synthesis of oligonucleotide-based drugs. It is also used to synthesize 2''-O-guanidinopropyl-modified nucleoside phosphoramidites to incorporate into siRNAs targeting hepatitis B virus.

Technology Process of N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 7 articles about N-Benzoyl-5'-O-(4,4-Dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]adenosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-N6-benzoyl adenosine (129681-71-6,81265-93-2) → N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (104992-55-4,131349-35-4,131432-30-9)

Guidance literature:

With pyridinium trifluroacetate; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1021/op990086k

Reference yield: 86.0%

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) + 5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-N6-benzoyl adenosine (129681-71-6,81265-93-2) → N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (104992-55-4,131349-35-4,131432-30-9)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 25 ℃; for 2h;

Reference yield: 85.0%

→ N6-benzoyl-5'-O-(4,4'-dimethoxytrityl)-2'-O-(tert-butyldimethylsilyl)adenosine 3'-O-(2-cyanoethyl N,N-diisopropylphosphoramidite) (104992-55-4,131349-35-4,131432-30-9)

Guidance literature:

upstream raw materials:

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

5'-O-dimethoxytrityl-2'-O-tert-butyldimethylsilyl-N₆-benzoyl adenosine

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

benzoyl chloride

Refernces

• 1、 Meher,Efthymiou,Stoop,Krishnamurthy. "Microwave-assisted preparation of nucleoside-phosphoramidites". supporting information. p. 7463 - 7465. Retrieved 2014/07/07.
• 2、 -. "Methods for synthesizing nucleosides, nucleoside derivatives and non-nucleoside derivatives". . . Retrieved 2008/06/13.