2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine

Base Information

• Chemical Name: 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine
• CAS No.: 1449578-46-4
• Molecular Formula: C₅₀H₆₁N₄O₁₂PS
• Molecular Weight: 973.094
• Mol file: 1449578-46-4.mol

Synonyms:2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine

Chemical Property of 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine

Chemical Property:

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine

There total 11 articles about 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine 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: 92.0%

2′-O-(2,4,6-trimethoxybenzylthiomethyl)-5′-O-(4,4′-dimethoxytrityl)uridine (1449578-45-3) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine (1449578-46-4)

Guidance literature:

With N,N-diisopropylammonium tetrazolide; In dichloromethane; at 20 ℃; for 15h;

DOI:10.1039/c3cc43725f

Reference yield: 88.0%

2′-O-(2,4,6-trimethoxybenzylthiomethyl)-5′-O-(4,4′-dimethoxytrityl)uridine (1449578-45-3) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine (1449578-46-4)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.bmc.2018.10.025

Reference yield:

3',5'-O-(di-tert-butylsilanediyl)-2'-O-(2,4,6-trimethoxybenzylthiomethyl)uridine (1449578-40-8) → 2′-O-(2,4,6-trimethoxybenzylthiomethyl)-3′-O-[(2-cyanoethyl)-(N,N-diisopropylamino)-phosphoramidyl]-5′-O-(4,4′-dimethoxytrityl)uridine (1449578-46-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 0.33 h / 20 °C

2: pyridine / 1.5 h / 20 °C

3: N,N-diisopropylammonium tetrazolide / dichloromethane / 15 h / 20 °C

With pyridine; triethylamine tris(hydrogen fluoride); N,N-diisopropylammonium tetrazolide; In tetrahydrofuran; dichloromethane;

DOI:10.1039/c3cc43725f

upstream raw materials:

3',5'-O-(di-tert-butylsilanediyl)-2'-O-(2,4,6-trimethoxybenzylthiomethyl)uridine

2′-O-(2,4,6-trimethoxybenzylthiomethyl)-5′-O-(4,4′-dimethoxytrityl)uridine

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

3’,5’-O-di-tert-silyl-2’-O-[(methylthio)methyl]uridine