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

Base Information

• Chemical Name: 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol
• CAS No.: 705967-70-0
• Molecular Formula: C₂₄H₃₃N₅O₅Si
• Molecular Weight: 499.642

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

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

Chemical Property:

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

There total 5 articles about 1,5-anhydro-2-(N⁶-benzoyladenin-9-yl)-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: 74.0%

1,5-anhydro-2-(N6-benzoyladenin-9-yl)-4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-69-7) → 1,5-anhydro-2-(N6-benzoyladenin-9-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-70-0)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1081/NCN-120028338

Reference yield:

1,5-anhydro-4,6-O-benzylidene-2-(N6-benzoyladenin-9-yl)-2-deoxy-D-altro-hexitol (705967-68-6) → 1,5-anhydro-2-(N6-benzoyladenin-9-yl)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-70-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / imidazole / dimethylformamide / 38 h / 70 °C

2: 74 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

With 1H-imidazole; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

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)-3-O-tert-butyldimethylsilyl-2-deoxy-D-altro-hexitol (705967-70-0)

Guidance literature:

Multi-step reaction with 4 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

4.1: 74 percent / trifluoroacetic acid / CH₂Cl₂ / 1 h / 20 °C

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

DOI:10.1081/NCN-120028338

upstream raw materials:

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

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

adenine

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

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