Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester

Base Information

• Chemical Name: Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester
• CAS No.: 190779-83-0
• Molecular Formula: C₂₁H₂₉N₅O₁₃P₂
• Molecular Weight: 621.434

Synonyms:

Chemical Property of Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester

There total 11 articles about Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester 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:

N-benzoyladenine (4005-49-6) → Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester (190779-83-0)

Guidance literature:

Multi-step reaction with 7 steps

1: pyridine / 6 h / Heating

2: 50 percent / TMSOTf / 1,2-dichloro-ethane / 16 h / Heating

3: 70 percent / t-BuOK / dioxane; methanol / 0.02 h / Ambient temperature

4: 96 percent / pyridine / 3 h / Ambient temperature

5: 1H-tetrazole / CH₂Cl₂; acetonitrile / 0.08 h / Ambient temperature

6: t-BuOOH / CH₂Cl₂; acetonitrile / 0.25 h / 0 °C

7: 1.) NaOH, 2.) aq. AcOH / 1.) 1,4-dioxane, MeOH, room temperature, 16 h, 2.) room temperature, 1 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; acetic acid; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00309-8

Reference yield:

N-Benzoyl-N,9-bis(trimethylsilyl)adenin (18055-47-5) → Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester (190779-83-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / TMSOTf / 1,2-dichloro-ethane / 16 h / Heating

2: 70 percent / t-BuOK / dioxane; methanol / 0.02 h / Ambient temperature

3: 96 percent / pyridine / 3 h / Ambient temperature

4: 1H-tetrazole / CH₂Cl₂; acetonitrile / 0.08 h / Ambient temperature

5: t-BuOOH / CH₂Cl₂; acetonitrile / 0.25 h / 0 °C

6: 1.) NaOH, 2.) aq. AcOH / 1.) 1,4-dioxane, MeOH, room temperature, 16 h, 2.) room temperature, 1 h

With pyridine; 1H-tetrazole; tert.-butylhydroperoxide; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; potassium tert-butylate; acetic acid; In 1,4-dioxane; methanol; dichloromethane; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00309-8

Reference yield:

Phosphorous acid (2S,3R,4R,5R,6R)-2-[2-(6-benzoylamino-purin-9-ylmethoxy)-ethoxy]-3-benzyloxy-5-[bis-(2-methanesulfonyl-ethoxy)-phosphanyloxy]-6-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-tetrahydro-pyran-4-yl ester bis-(2-methanesulfonyl-ethyl) ester → Phosphoric acid mono-{(2R,3R,4R,5R,6S)-6-[2-(6-amino-purin-9-ylmethoxy)-ethoxy]-5-benzyloxy-2-hydroxymethyl-4-phosphonooxy-tetrahydro-pyran-3-yl} ester (190779-83-0)

Guidance literature:

Multi-step reaction with 2 steps

1: t-BuOOH / CH₂Cl₂; acetonitrile / 0.25 h / 0 °C

2: 1.) NaOH, 2.) aq. AcOH / 1.) 1,4-dioxane, MeOH, room temperature, 16 h, 2.) room temperature, 1 h

With tert.-butylhydroperoxide; sodium hydroxide; acetic acid; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(97)00309-8

upstream raw materials:

N-benzoyladenine

N-Benzoyl-N,9-bis(trimethylsilyl)adenin

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-(2-hydroxy-ethoxy)-tetrahydro-pyran-4-yl ester

Acetic acid (2R,3R,4S,5R,6S)-3-acetoxy-2-acetoxymethyl-5-benzyloxy-6-(2-methylsulfanylmethoxy-ethoxy)-tetrahydro-pyran-4-yl ester

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