1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Base Information

• Chemical Name: 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol
• CAS No.: 705967-69-7
• Molecular Formula: C₃₁H₃₇N₅O₅Si
• Molecular Weight: 587.751

Synonyms:1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Chemical Property of 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

There total 4 articles about 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol 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: 68.0%

1,5-anhydro-4,6-O-benzylidene-2-(N6-benzoyladenin-9-yl)-2-deoxy-D-altro-hexitol (705967-68-6) + tert-butyldimethylsilyl chloride (18162-48-6) → 1,5-anhydro-2-(N6-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-69-7)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 70 ℃; for 38h;

DOI:10.1081/NCN-120028338

Reference yield:

adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → 1,5-anhydro-2-(N6-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hydride; 12-crown-4 / dimethylformamide / 1.5 h / 120 °C

1.2: 80 percent / dimethylformamide / 1 h / 120 °C

2.1: trimethylsilyl chloride; pyridine / 1 h / 20 °C

2.2: 2 h / 20 °C

2.3: 79 percent / TBAF / tetrahydrofuran / 0.08 h / 20 °C

3.1: 68 percent / imidazole / dimethylformamide / 38 h / 70 °C

With pyridine; 1H-imidazole; chloro-trimethyl-silane; (1,4,7,10-tetraoxacyclododecane); lithium hydride; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120028338

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(adenin-9-yl)-D-altro-hexitol (705967-67-5) → 1,5-anhydro-2-(N6-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-69-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: trimethylsilyl chloride; pyridine / 1 h / 20 °C

1.2: 2 h / 20 °C

1.3: 79 percent / TBAF / tetrahydrofuran / 0.08 h / 20 °C

2.1: 68 percent / imidazole / dimethylformamide / 38 h / 70 °C

With pyridine; 1H-imidazole; chloro-trimethyl-silane; In N,N-dimethyl-formamide;

DOI:10.1081/NCN-120028338

upstream raw materials:

1,5-anhydro-4,6-O-benzylidene-2-(N⁶-benzoyladenin-9-yl)-2-deoxy-D-altro-hexitol

tert-butyldimethylsilyl chloride

adenine

1,5-anhydro-4,6-O-benzylidene-2-deoxy-2-(adenin-9-yl)-D-altro-hexitol

Downstream raw materials:

1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol

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