2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Base Information

• Chemical Name: 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS No.: 226917-55-1
• Molecular Formula: C₄₁H₆₅N₇O₈Si
• Molecular Weight: 812.095

Synonyms:2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Chemical Property of 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Chemical Property:

Purity/Quality:

98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

There total 19 articles about 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine 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: 89.0%

2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-54-0) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-55-1)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; dichloromethane; for 0.5h; Ambient temperature;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

Reference yield:

(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5(hydroxymethyl)tetrahydrofuran-3-ol (37731-73-0) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-55-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 89 percent / pyridine / 19 h / Ambient temperature

2: 93 percent / Et₃N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature

3: 10 percent / NaH / dimethylformamide / 1.) -5 to 0 deg C, 1 h; 2.) RT, 30 min

4: 69 percent / H₂ / 5 percent Pd/C / aq. ethanol / 96 h / 760 Torr

5: 93 percent / dimethylformamide / 2 h / Ambient temperature

6: CH₂Cl₂ / 0.83 h / Ambient temperature

7: CH₂Cl₂ / Ambient temperature

8: Et₃N / 3 h / Ambient temperature

9: 88 percent / pyridine / 19 h / Ambient temperature

10: 95 percent / 1H-imidazole / pyridine / 48 h / Ambient temperature

11: 89 percent / 2 percent TsOH / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

Reference yield:

9-<2,3-anhydro-5-O-<(tert-butyl)diphenylsilyl>-β-D-ribofuranosyl>adenine (125084-70-0) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-55-1)

Guidance literature:

Multi-step reaction with 11 steps

1: 90 percent / Et₃N, (CH₃)2BBr / CH₂Cl₂ / 0.25 h / -78 °C

2: 93 percent / Et₃N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature

3: 10 percent / NaH / dimethylformamide / 1.) -5 to 0 deg C, 1 h; 2.) RT, 30 min

4: 69 percent / H₂ / 5 percent Pd/C / aq. ethanol / 96 h / 760 Torr

5: 93 percent / dimethylformamide / 2 h / Ambient temperature

6: CH₂Cl₂ / 0.83 h / Ambient temperature

7: CH₂Cl₂ / Ambient temperature

8: Et₃N / 3 h / Ambient temperature

9: 88 percent / pyridine / 19 h / Ambient temperature

10: 95 percent / 1H-imidazole / pyridine / 48 h / Ambient temperature

11: 89 percent / 2 percent TsOH / CH₂Cl₂; methanol / 0.5 h / Ambient temperature

With pyridine; 1H-imidazole; dimethylboron bromide; hydrogen; sodium hydride; toluene-4-sulfonic acid; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/(SICI)1522-2675(19990407)82:4<597::AID-HLCA597>3.0.CO;2-V

upstream raw materials:

2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5(hydroxymethyl)tetrahydrofuran-3-ol

9-[3-(benzylamino)-3-deoxy-β-D-ribofuranosyl]adenine

9-(2,3-anhydro-β-D-ribofuranosyl)adenine

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