N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate

Base Information

• Chemical Name: N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate
• CAS No.: 263709-06-4
• Molecular Formula: C₃₅H₄₇N₇O₁₃Si
• Molecular Weight: 801.883

Synonyms:N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate

Chemical Property of N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate

Chemical Property:

Purity/Quality:

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MSDS Files:

Useful:

Technology Process of N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate

There total 4 articles about N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate 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:

2-(4-nitrophenyl)ethanol (100-27-6) → N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate (263709-06-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 63 percent / 17 h / 105 °C

2: 95 percent / pyridine; 1H-imidazole / 17 h / 20 °C

3: toluene / 17 h / 80 °C

With pyridine; 1H-imidazole; In toluene; 1: Esterification / 2: Etherification / 3: Addition;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

Reference yield:

L-threonine 2-(4-nitrophenyl)ethyl ester 4-methylbenzenesulfonate salt → N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate (263709-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine; 1H-imidazole / 17 h / 20 °C

2: toluene / 17 h / 80 °C

With pyridine; 1H-imidazole; In toluene; 1: Etherification / 2: Addition;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

Reference yield:

O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester (263709-00-8) + Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-isocyanato-purin-9-yl)-tetrahydro-furan-3-yl ester (263709-04-2) → N6-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine 2',3',5'-triacetate (263709-06-4)

Guidance literature:

In toluene; at 80 ℃; for 17h;

DOI:10.1002/(SICI)1522-2675(20000119)83:1<152::AID-HLCA152>3.0.CO;2-1

upstream raw materials:

O-[(tert-butyl)dimethylsilyl]-L-threonine 2-(4-nitrophenyl)ethyl ester

Acetic acid (2R,3R,4R,5R)-4-acetoxy-5-acetoxymethyl-2-(6-isocyanato-purin-9-yl)-tetrahydro-furan-3-yl ester

2-(4-nitrophenyl)ethanol

2',3',5'-tri-O-acetyl-N⁶-(phenoxycarbonyl)adenosine

Downstream raw materials:

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}adenosine

N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

2'-O-[(tert-butyl)dimethylsilyl]-N⁶-{{{(1S,2R)-2-{[(tert-butyl)dimethylsilyl]oxy}-1-{[2-(4-nitrophenyl)ethoxy]carbonyl}propyl}amino}carbonyl}-5'-O-(4,4'-dimethoxytrityl)adenosine

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