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

Base Information

• Chemical Name: 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-benzyloxypurine ribonucleoside
• CAS No.: 1393526-56-1
• Molecular Formula: C₃₀H₄₈FN₅O₄Si₂
• Molecular Weight: 617.912
• Mol file: 1393526-56-1.mol

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

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

There total 3 articles about 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-benzyloxypurine 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: 50.0%

(2R,3R,4R,5R)-5-(2-amino-6-(benzyloxy)-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol (1199809-29-4) + tert-butyldimethylsilyl chloride (18162-48-6) → 3′,5′-bis-O-tert-butyldimethylsilyl-2′-deoxy-2′-α-fluoro-2′-β-C-methyl-2-amino-6-benzyloxypurine ribonucleoside (1393526-56-1)

Guidance literature:

With pyridine; at 20 ℃; for 18h; Inert atmosphere;

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-2-amino-6-benzyloxypurine ribonucleoside (1393526-56-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; 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-2-amino-6-benzyloxypurine ribonucleoside (1393526-56-1)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1021/ol301937v

upstream raw materials:

tert-butyldimethylsilyl chloride

(2R,3R,4R,5R)-5-(2-amino-6-(benzyloxy)-9H-purin-9-yl)-4-fluoro-2-(hydroxymethyl)-4-methyltetrahydrofuran-3-ol

Downstream raw materials:

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

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

C₄₄H₅₆FN₅O₆Si₂

C₃₈H₄₂FN₅O₆Si