5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE

Base Information

• Chemical Name: 5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE
• CAS No.: 134031-86-0
• Molecular Formula: C40H49N4O8P
• Molecular Weight: 760.81
• Hs Code.: 29349990
• Mol file: 134031-86-0.mol

Synonyms:5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE

Chemical Property of 5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE

Chemical Property:

• PKA: 9.55±0.10(Predicted)
• PSA: 150.86000
• LogP: 6.81958
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

97% ^*data from raw suppliers

5''-O-[(N,N-diisopropylamino)-(2-cyanoethoxy)phosphinyl]-3''-O-(4,4''-dimethoxytrityl)-thymidine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 2'-OMe-U Phosphoramidite can be for incorporation of an (otherwise unmodified) reverse (5' to 3') dT nucleobase within an oligonucleotide.

Technology Process of 5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE

There total 8 articles about 5'-O-[(N,N-DIISOPROPYLAMINO)-(2-CYANOETHOXY)PHOSPHINYL]-3'-O-(4,4'-DIMETHOXYTRITYL)-THYMIDINE 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: 73.0%

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) + 3'-O-(4,4'-dimethoxytrityl)thymidine (76054-81-4) → 3’-(4,4’-dimethoxytrityl)-thymidine 5’-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (134031-86-0)

Guidance literature:

With 1H-tetrazole; In acetonitrile;

DOI:10.1080/07328319708006249

Reference yield:

4,4'-dimethoxytrityl chloride (40615-36-9) → 3’-(4,4’-dimethoxytrityl)-thymidine 5’-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (134031-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine / CH₂Cl₂ / 2 h / 60 °C

2: 90 percent / DBU / acetonitrile / 2 h / 20 °C

3: 73 percent / 1H-tetrazole / acetonitrile / 1 h

With pyridine; 1H-tetrazole; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; acetonitrile; 1: Condensation / 2: Elimination / 3: phosphitylation;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

Reference yield:

5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine (123533-02-8) → 3’-(4,4’-dimethoxytrityl)-thymidine 5’-[(2-cyanoethyl)-(N,N-diisopropyl)]phosphoramidite (134031-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / pyridine / 2 h / 60 °C

2: 96 percent / (Bu₄N)F*H₂O; AcOH / tetrahydrofuran / 20 °C

3: 73 percent / 1H-tetrazole / acetonitrile / 1 h

With pyridine; 1H-tetrazole; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; acetonitrile; 1: Condensation / 2: desilylation / 3: phosphitylation;

DOI:10.1002/1522-2675(20000809)83:8<2023::AID-HLCA2023>3.0.CO;2-P

upstream raw materials:

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

3'-O-(4,4'-dimethoxytrityl)thymidine

4,4'-dimethoxytrityl chloride

5'-O-[dimethyl(1,1,2-trimethylpropyl)silyl]thymidine

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