9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine

Base Information

• Chemical Name: 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine
• CAS No.: 418767-00-7
• Molecular Formula: C₄₄H₄₆N₅O₁₅P₃
• Molecular Weight: 977.795

Synonyms:9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine

Chemical Property of 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine

Chemical Property:

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Technology Process of 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine

There total 10 articles about 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ⁵-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine 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%

2-(N,N-diisopropylamino)-5,6-benzo-1,3,2-dioxaphosphepane (132741-50-5) + [(2S)-3-(6-amino-9H-purin-9-yl)-2-hydroxypropyl] 2-O-benzyl-α-D-xylopyranoside (418766-97-9) → 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine (418767-00-7)

Guidance literature:

2-(N,N-diisopropylamino)-5,6-benzo-1,3,2-dioxaphosphepane; [(2S)-3-(6-amino-9H-purin-9-yl)-2-hydroxypropyl] 2-O-benzyl-α-D-xylopyranoside; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 4h;

With tert.-butylhydroperoxide; In dichloromethane; water; at 0 - 20 ℃; for 0.25h;

DOI:10.1016/S0968-0896(01)00329-7

Reference yield:

allyl 3,4-di-O-benzoyl-2-O-benzyl-α-D-xylopyranoside (196859-39-9) → 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine (418767-00-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: TFA / 10 percent Pd/C / dioxane; H₂O / 20 h / Heating

1.2: K₂CO₃; Cl₃CCN / CH₂Cl₂ / 12 h / 20 °C

1.3: 4 Angstroem MS; TMSOTf / CH₂Cl₂ / 0.75 h / -20 °C

2.1: NaH / dimethylformamide / 1.5 h / 80 °C

2.2: dimethylformamide / 3 h / 80 °C

3.1: 95 percent / MeONa / methanol

4.1: 1H-tetrazole / CH₂Cl₂ / 4 h / 20 °C

4.2: 74 percent / t-BuOOH / CH₂Cl₂; H₂O / 0.25 h / 0 - 20 °C

With 1H-tetrazole; sodium methylate; sodium hydride; trifluoroacetic acid; palladium on activated charcoal; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0968-0896(01)00329-7

Reference yield:

2-(N,N-diisopropylamino)-5,6-benzo-1,3,2-dioxaphosphepane (132741-50-5) + [2-hydroxy-3-(6-amino-9H-purin-9-yl)propyl] 2-O-benzyl-3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside (418766-81-1) → 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine (418767-00-7) + 9-[3-[3-benzyloxy-4,5-bis-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-tetrahydro-pyran-2-yloxy]-2-(3-oxo-1,5-dihydro-3λ5-benzo[e][1,3,2]dioxaphosphepin-3-yloxy)-propyl]-9H-purin-6-ylamine (418766-90-2)

Guidance literature:

[2-hydroxy-3-(6-amino-9H-purin-9-yl)propyl] 2-O-benzyl-3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.166667h;

2-(N,N-diisopropylamino)-5,6-benzo-1,3,2-dioxaphosphepane; With 1H-tetrazole; In dichloromethane; at 20 ℃; for 4h;

With tert.-butylhydroperoxide; In dichloromethane; water; at 0 - 20 ℃; for 0.25h;

DOI:10.1016/S0968-0896(01)00329-7

upstream raw materials:

2-(N,N-diisopropylamino)-5,6-benzo-1,3,2-dioxaphosphepane

[(2S)-3-(6-amino-9H-purin-9-yl)-2-hydroxypropyl] 2-O-benzyl-α-D-xylopyranoside

[2-hydroxy-3-(6-amino-9H-purin-9-yl)propyl] 2-O-benzyl-3,4-O-[(2S,3S)-(2,3-dimethoxybutane-2,3-diyl)]-α-D-xylopyranoside

benzyl bromide

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