N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-6'-O-methylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Base Information

• Chemical Name: N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-6'-O-methylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite
• CAS No.: 153248-58-9
• Molecular Formula: C₄₉H₆₆N₇O₉PSi
• Molecular Weight: 956.164
• Mol file: 153248-58-9.mol

Synonyms:5'-O-DMT-2'-TBDMS-6'-O-Me-rG(N-Ac)-3'-CEDPA

Chemical Property of N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-6'-O-methylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

Chemical Property:

• PSA: 187.16000
• LogP: 9.84118

Purity/Quality:

97% ^*data from raw suppliers

N-Acetyl-2'-O-[(tert-butyl)dimethylsilyl]-5'-O-DMT-6'-O-methylguanosine-3'-CE phosphoramidite ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Technology Process of N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-6'-O-methylguanosine-3'-(2-cyanoethyl-N,N-diisopropyl)phosphoramidite

There total 7 articles about N-Acetyl-5'-O-(4,4-dimethoxytrityl)-2'-O-[(tert-butyl)dimethylsilyl]-6'-O-methylguanosine-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: 53.0%

N-(9-((2R,3R,4R,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3-((tertbutyldimethylsilyl)oxy)-4-hydroxytetrahydrofuran-2-yl)-6-methoxy-9H-purin-2-yl)acetamide + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → (2R,3R,4R,5R)-5-(2-acetamido-6-methoxy-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl but-3-yn-1-yl diisopropylphosphoramidite (153248-58-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.75h;

DOI:10.1021/jacs.7b07914

Reference yield:

2-Amino-6-chloropurine riboside (2004-07-1) → (2R,3R,4R,5R)-5-(2-acetamido-6-methoxy-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl but-3-yn-1-yl diisopropylphosphoramidite (153248-58-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: methanol / 12 h / Reflux

2.1: pyridine / 16 h / 70 °C

3.1: triethylamine / methanol; water / 2 h / 20 °C

4.1: N,N-dimethyl-formamide / 1 h / 0 - 20 °C

4.2: 0.25 h / 20 °C

5.1: pyridine; 1H-imidazole / 16 h / 20 °C

6.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C

7.1: pyridine; dmap / 16 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jacs.7b07914

Reference yield:

6-O-methylguanosine (7803-88-5) → (2R,3R,4R,5R)-5-(2-acetamido-6-methoxy-9H-purin-9-yl)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)tetrahydrofuran-3-yl but-3-yn-1-yl diisopropylphosphoramidite (153248-58-9)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine / 16 h / 70 °C

2.1: triethylamine / methanol; water / 2 h / 20 °C

3.1: N,N-dimethyl-formamide / 1 h / 0 - 20 °C

3.2: 0.25 h / 20 °C

4.1: pyridine; 1H-imidazole / 16 h / 20 °C

5.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 0.5 h / 0 - 20 °C

6.1: pyridine; dmap / 16 h / 20 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.75 h / 0 °C

With pyridine; 1H-imidazole; dmap; pyridine hydrogenfluoride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jacs.7b07914

upstream raw materials:

2-Amino-6-chloropurine riboside

6-O-methylguanosine

(2R,3R,4R,5R)-2-(2-acetamido-6-methoxy-9H-purin-9-yl)-5-(acetoxymethyl)tetrahydrofuran-3,4-diyl diacetate

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

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