3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside

Base Information

• Chemical Name: 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside
• CAS No.: 1393526-54-9
• Molecular Formula: C₄₀H₆₄FN₅O₈Si₂
• Molecular Weight: 818.146
• Mol file: 1393526-54-9.mol

Synonyms:3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside

Chemical Property of 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside

There total 4 articles about 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside 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: 87.0%

di-tert-butyl dicarbonate (24424-99-5) + 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-benzyloxypurine ribonucleoside (1393526-56-1) → 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N2-bis-tertbutylcarbonatepurine ribonucleoside (1393526-54-9)

Guidance literature:

With dmap; In tetrahydrofuran; at 20 ℃; for 3h;

DOI:10.1021/ol301937v

Reference yield:

(2R,3R,4R,5R)-5-(2-amino-6-chloro-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol → 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N2-bis-tertbutylcarbonatepurine ribonucleoside (1393526-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran / 1 h / 20 °C

3: dmap / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; dmap; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol301937v

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N2-bis-tertbutylcarbonatepurine ribonucleoside (1393526-54-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1H-imidazole / N,N-dimethyl-formamide / 20 °C / Inert atmosphere

2: sodium hydride / tetrahydrofuran / 1 h / 20 °C

3: dmap / tetrahydrofuran / 3 h / 20 °C

With 1H-imidazole; dmap; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol301937v

upstream raw materials:

3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-chloro-purine ribonucleoside

di-tert-butyl dicarbonate

3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-benzyloxypurine ribonucleoside

tert-butyldimethylsilyl chloride

Downstream raw materials:

3′-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-6-benzyloxy-N²-bis-tertbutylcarbonatepurine ribonucleoside