2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine

Base Information

• Chemical Name: 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine
• CAS No.: 1384524-73-5
• Molecular Formula: C₃₈H₄₅N₉O₆Si
• Molecular Weight: 751.918
• Mol file: 1384524-73-5.mol

Synonyms:

Chemical Property of 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine

There total 10 articles about 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine 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: 71.0%

1,2-di-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-α-D-ribofuranose (1384524-69-9) + N2-acetyl-O6-(diphenylcarbamoyl)guanine (112233-74-6) → 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine (1384524-73-5)

Guidance literature:

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine; With N,O-bis-(trimethylsilyl)-acetamide; In 1,2-dichloro-ethane; for 0.5h; Reflux; Inert atmosphere;

1,2-di-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-α-D-ribofuranose; With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; for 2h; stereoselective reaction; Reflux; Inert atmosphere;

DOI:10.1246/cl.2012.403

Reference yield:

3-azido-3,5-dideoxy-1,2-O-isopropylidene-5-(triisopropylsilyl)ethynyl-α-D-ribofuranose → 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine (1384524-73-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: trifluoroacetic acid / water / 6 h / 20 °C / Air

2.1: dmap; triethylamine / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

3.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux; Inert atmosphere

3.2: 2 h / Reflux; Inert atmosphere

With dmap; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; trifluoroacetic acid; In dichloromethane; water; 1,2-dichloro-ethane;

DOI:10.1246/cl.2012.403

Reference yield:

C16H29N3O3Si → 2-(acetylamino)-9-[2-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-β-D-ribofuranosyl]-6-(diphenylcarbamoyloxy)-9H-purine (1384524-73-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / dichloromethane / 0.67 h / 0 - 20 °C / Inert atmosphere

2.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / Reflux; Inert atmosphere

2.2: 2 h / Reflux; Inert atmosphere

With dmap; N,O-bis-(trimethylsilyl)-acetamide; triethylamine; In dichloromethane; 1,2-dichloro-ethane;

DOI:10.1246/cl.2012.403

upstream raw materials:

D-xylofuranose

1,2-di-O-acetyl-3-azido-3,5-dideoxy-5-(triisopropylsilyl)ethynyl-α-D-ribofuranose

N₂-acetyl-O₆-(diphenylcarbamoyl)guanine

3,5-anhydro-1,2-O-isopropylidene-α-D-xylofuranose