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

Base Information

• Chemical Name: 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS No.: 226917-54-0
• Molecular Formula: C₆₁H₈₁N₇O₉Si
• Molecular Weight: 1084.44
• Mol file: 226917-54-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 18 articles about 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-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: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-53-9) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-54-0)

Guidance literature:

With 1H-imidazole; In pyridine; for 48h; 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)-5'-O-(monomethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-54-0)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-imidazole; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; 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-<3-bromo-5-O-<(tert-butyl)diphenylsilyl>-3-deoxy-β-D-xylofuranosyl>adenine (125084-68-6) → 2'-O-<(tert-butyl)dimethylsilyl>-3'-deoxy-3'-(hexadecanoylamino)-5'-O-(monomethoxytrityl)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-54-0)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / Et₃N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature

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

3: 69 percent / H₂ / 5 percent Pd/C / aq. ethanol / 96 h / 760 Torr

4: 93 percent / dimethylformamide / 2 h / Ambient temperature

5: CH₂Cl₂ / 0.83 h / Ambient temperature

6: CH₂Cl₂ / Ambient temperature

7: Et₃N / 3 h / Ambient temperature

8: 88 percent / pyridine / 19 h / Ambient temperature

9: 95 percent / 1H-imidazole / pyridine / 48 h / Ambient temperature

With pyridine; 1H-imidazole; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; 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:

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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