3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine

Base Information

• Chemical Name: 3'-deoxy-3'-(hexadecanoylamino)-N⁶-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine
• CAS No.: 226917-51-7
• Molecular Formula: C₃₅H₅₁N₇O₈
• Molecular Weight: 697.832
• Mol file: 226917-51-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 16 articles about 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:

(2R,3S,4R,5R)-2-(6-amino-9H-purin-9-yl)-4-bromo-5(hydroxymethyl)tetrahydrofuran-3-ol (37731-73-0) → 3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-51-7)

Guidance literature:

Multi-step reaction with 8 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

With pyridine; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 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) → 3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-51-7)

Guidance literature:

Multi-step reaction with 8 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

With dimethylboron bromide; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 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-β-D-ribofuranosyl)adenine (2627-64-7) → 3'-deoxy-3'-(hexadecanoylamino)-N6-<2-(4-nitrophenyl)ethoxycarbonyl>adenosine (226917-51-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 87 percent / pyridine / 16 h / Ambient temperature

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

3: 93 percent / Et₃N / tetrahydrofuran; acetonitrile / 72 h / Ambient temperature

4: 10 percent / NaH / dimethylformamide / 1.) -5 to 0 deg C, 1 h; 2.) RT, 30 min

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

6: 93 percent / dimethylformamide / 2 h / Ambient temperature

7: CH₂Cl₂ / 0.83 h / Ambient temperature

8: CH₂Cl₂ / Ambient temperature

9: Et₃N / 3 h / Ambient temperature

With pyridine; dimethylboron bromide; hydrogen; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 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:

methanol

(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

Downstream raw materials:

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

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

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