9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

Base Information

• Chemical Name: 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine
• CAS No.: 148313-18-2
• Molecular Formula: C₅₇H₅₂N₈O₁₇
• Molecular Weight: 1121.08

Synonyms:9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

Chemical Property of 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

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Technology Process of 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

There total 10 articles about 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N²-<2-(4-nitrophenyl)ethoxycarbonyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine 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: 89.0%

4,4'-dimethoxytrityl chloride (40615-36-9) + N2-<2-(4-nitrophenyl)ethoxycarbonyl>-9-<2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-O6-<2-(4-nitrophenyl)ethyl>guanine (148313-10-4) → 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N2-<2-(4-nitrophenyl)ethoxycarbonyl>-O6-<2-(4-nitrophenyl)ethyl>guanine (148313-18-2)

Guidance literature:

With pyridine; for 24h; Ambient temperature;

DOI:10.1002/hlca.19930760110

Reference yield:

9-β-D-arabinofuranosylguanine (38819-10-2) → 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N2-<2-(4-nitrophenyl)ethoxycarbonyl>-O6-<2-(4-nitrophenyl)ethyl>guanine (148313-18-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 94 percent / pyridine / dimethylformamide / 5 h / Ambient temperature

2: PPh₃ / dioxane / 0.75 h / Ambient temperature

3: diethyl azodicarboxylate / 4 h

4: 94 percent / pyridine / Ambient temperature

5: 82 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 22 h / Ambient temperature

6: pyridine / 24 h / Ambient temperature

7: 68 percent / AcOH, (Bu₄N)F*3H₂O / tetrahydrofuran / 3.5 h / Ambient temperature

8: 89 percent / pyridine / 24 h / Ambient temperature

With pyridine; dmap; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/hlca.19930760110

Reference yield:

9-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)guanine (74491-89-7) → 9-<5'-O-(dimethoxytrityl)-2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-N2-<2-(4-nitrophenyl)ethoxycarbonyl>-O6-<2-(4-nitrophenyl)ethyl>guanine (148313-18-2)

Guidance literature:

Multi-step reaction with 7 steps

1: PPh₃ / dioxane / 0.75 h / Ambient temperature

2: diethyl azodicarboxylate / 4 h

3: 94 percent / pyridine / Ambient temperature

4: 82 percent / 4-(dimethylamino)pyridine / CH₂Cl₂ / 22 h / Ambient temperature

5: pyridine / 24 h / Ambient temperature

6: 68 percent / AcOH, (Bu₄N)F*3H₂O / tetrahydrofuran / 3.5 h / Ambient temperature

7: 89 percent / pyridine / 24 h / Ambient temperature

With pyridine; dmap; tetrabutyl ammonium fluoride; acetic acid; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; 1,4-dioxane; dichloromethane;

DOI:10.1002/hlca.19930760110

upstream raw materials:

4,4'-dimethoxytrityl chloride

N²-<2-(4-nitrophenyl)ethoxycarbonyl>-9-<2'-O-<2-(4-nitrophenyl)ethoxycarbonyl>-β-D-arabinofuranosyl>-O⁶-<2-(4-nitrophenyl)ethyl>guanine

9-β-D-arabinofuranosylguanine

9-(2',3',5'-tri-O-acetyl-β-D-arabinofuranosyl)guanine

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