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

Base Information

• Chemical Name: 2-chloro-N⁶-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-β-D-ribofuranosyl)adenine
• CAS No.: 889126-22-1
• Molecular Formula: C₃₀H₄₇ClIN₇O₄Si₂
• Molecular Weight: 788.276

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

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

Chemical Property:

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

There total 9 articles about 2-chloro-N⁶-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-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: 91.0%

2-chloro-N6-(3-iodobenzyl)-9-[3-(3-chloroacetylureido)-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl]adenine (889126-19-6) → 2-chloro-N6-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-β-D-ribofuranosyl)adenine (889126-22-1)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 18h;

DOI:10.1021/jm050968b

Reference yield:

Acetic acid (2S,3S,4R)-3-azido-4,5-dihydroxy-tetrahydro-furan-2-ylmethyl ester → 2-chloro-N6-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-β-D-ribofuranosyl)adenine (889126-22-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 2 g / pyridine / 16 h / 20 °C

2.1: HMDS; ammonium sulfate / 16 h / Heating

2.2: 51 percent / TMSOTf / 1,2-dichloro-ethane / 2.33 h / 20 - 60 °C

3.1: Et₃N / ethanol / 18 h / 50 °C

3.2: 95 percent / NaOMe / methanol / 2 h / 20 °C

4.1: 83 percent / imidazole / dimethylformamide / 24 h / 20 °C

5.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

5.2: 94 percent / aq. NH₄OH / tetrahydrofuran / 20 °C

6.1: 81 percent / dimethylformamide / 2 h / 0 °C

7.1: 91 percent / NaOMe / methanol / 18 h / 20 °C

With pyridine; 1H-imidazole; ammonium sulfate; sodium methylate; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm050968b

Reference yield:

5-O-acetyl-3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (889126-05-0) → 2-chloro-N6-(3-iodobenzyl)-9-(2,5-di-O-t-butyldimethylsilyl-3-deoxy-3-ureido-β-D-ribofuranosyl)adenine (889126-22-1)

Guidance literature:

Multi-step reaction with 8 steps

1.1: aq. formic acid / 1.5 h / 60 °C

2.1: 2 g / pyridine / 16 h / 20 °C

3.1: HMDS; ammonium sulfate / 16 h / Heating

3.2: 51 percent / TMSOTf / 1,2-dichloro-ethane / 2.33 h / 20 - 60 °C

4.1: Et₃N / ethanol / 18 h / 50 °C

4.2: 95 percent / NaOMe / methanol / 2 h / 20 °C

5.1: 83 percent / imidazole / dimethylformamide / 24 h / 20 °C

6.1: triphenylphosphine / tetrahydrofuran / 0.5 h / 0 °C

6.2: 94 percent / aq. NH₄OH / tetrahydrofuran / 20 °C

7.1: 81 percent / dimethylformamide / 2 h / 0 °C

8.1: 91 percent / NaOMe / methanol / 18 h / 20 °C

With pyridine; 1H-imidazole; ammonium sulfate; formic acid; sodium methylate; triethylamine; triphenylphosphine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; methanol; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm050968b

upstream raw materials:

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

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

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

9-(2,5-di-O-acetyl-3-azido-3-deoxy-β-D-ribofuranosyl)-2,6-dichloropurine

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