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

Base Information

• Chemical Name: 2-chloro-N⁶-(3-iodobenzyl)-9-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine
• CAS No.: 889126-13-0
• Molecular Formula: C₂₉H₄₄ClIN₈O₃Si₂
• Molecular Weight: 771.249

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

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

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

There total 6 articles about 2-chloro-N⁶-(3-iodobenzyl)-9-(3-azido-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: 83.0%

2-chloro-N6-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine (889126-10-7) + tert-butyldimethylsilyl chloride (18162-48-6) → 2-chloro-N6-(3-iodobenzyl)-9-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine (889126-13-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

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-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine (889126-13-0)

Guidance literature:

Multi-step reaction with 4 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

With pyridine; 1H-imidazole; ammonium sulfate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In 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-(3-azido-2,5-di-O-t-butyldimethylsilyl-3-deoxy-β-D-ribofuranosyl)adenine (889126-13-0)

Guidance literature:

Multi-step reaction with 5 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

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

DOI:10.1021/jm050968b

upstream raw materials:

2-chloro-N⁶-(3-iodobenzyl)-9-(3-azido-3-deoxy-β-D-ribofuranosyl)adenine

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

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

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

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

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