N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine

Base Information

• Chemical Name: N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine
• CAS No.: 889126-18-5
• Molecular Formula: C₃₂H₄₉ClIN₇O₅Si₂
• Molecular Weight: 830.313

Synonyms:N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine

Chemical Property of N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine

There total 8 articles about N⁶-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine 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: 77.0%

N6-(3-iodobenzyl)-9-(3-amino-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine (889126-15-2) + 2-chloroacetylisocyanate (4461-30-7) → N6-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine (889126-18-5)

Guidance literature:

In N,N-dimethyl-formamide; at 0 ℃; for 2h;

DOI:10.1021/jm050968b

Reference yield:

1,2,5-tri-O-acetyl-3-azido-3-deoxy-D-ribofuranose (179530-74-6) → N6-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine (889126-18-5)

Guidance literature:

Multi-step reaction with 6 steps

1: TMSOTf / 1,2-dichloro-ethane / 0 - 60 °C

2: Et₃N / ethanol

3: NaOMe; MeOH

4: imidazole / dimethylformamide

5: triphenylphosphine; aqueous ammonia / tetrahydrofuran

6: dimethylformamide

With 1H-imidazole; methanol; ammonium hydroxide; sodium methylate; triethylamine; triphenylphosphine; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; ethanol; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060079

Reference yield:

N6-(3-iodobenzyl)-9-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine (889126-12-9) → N6-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine (889126-18-5)

Guidance literature:

Multi-step reaction with 2 steps

1: triphenylphosphine; aqueous ammonia / tetrahydrofuran

2: dimethylformamide

With ammonium hydroxide; triphenylphosphine; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1081/NCN-200060079

upstream raw materials:

N⁶-(3-iodobenzyl)-9-(3-amino-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine

2-chloroacetylisocyanate

1,2,5-tri-O-acetyl-3-azido-3-deoxy-D-ribofuranose

N⁶-(3-iodobenzyl)-9-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine

Downstream raw materials:

N⁶-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-β-D-ribofuranosyl)adenine

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