[(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol

Base Information

• Chemical Name: [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol
• CAS No.: 380488-83-5
• Molecular Formula: C₁₉H₂₁N₅O₃
• Molecular Weight: 367.407

Synonyms:[(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol

Chemical Property of [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol

Chemical Property:

Purity/Quality:

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Technology Process of [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol

There total 10 articles about [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol 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: 54.0%

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) + (1S,2R)-5-(4-methoxyphenylmethoxy)-1,3-dioxabicyclo[4.3.0]non-7-en-2-one (380488-82-4) → [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol (380488-83-5)

Guidance literature:

tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dimethyl sulfoxide; at 45 ℃; for 2h;

DOI:10.1021/jo010718c

Reference yield:

p-Methoxybenzyl bromide (2746-25-0) → [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol (380488-83-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 86 percent / NaH / tetrahydrofuran / 6 h / 20 °C

2.1: 75 percent / 0.8percent H₂SO₄ / methanol / 10 h / 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: 64 percent / NaI / butan-2-one / 8 h / Heating

5.1: 80 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

6.1: 3.17 g / 0.4percent H₂SO₄ / dioxane / 2 h / Heating

7.1: NaIO₄; SiO₂ / CH₂Cl₂ / 1 h / 20 °C

7.2: 70 percent / NaBH₄ / methanol / 1 h / 20 °C

8.1: 69 percent / benzene / 4 h / Heating

9.1: 54 percent / Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h / 45 °C

With dmap; sodium periodate; silica gel; sodium hydride; triethylamine; sodium iodide; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; butanone; benzene;

DOI:10.1021/jo010718c

Reference yield:

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (175877-45-9) → [(1R,4R)-4-(6-Amino-purin-9-yl)-1-(4-methoxy-benzyloxy)-cyclopent-2-enyl]-methanol (380488-83-5)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 86 percent / NaH / tetrahydrofuran / 6 h / 20 °C

2.1: 75 percent / 0.8percent H₂SO₄ / methanol / 10 h / 20 °C

3.1: Et₃N; DMAP / CH₂Cl₂ / 1 h / 20 °C

4.1: 64 percent / NaI / butan-2-one / 8 h / Heating

5.1: 80 percent / Grubbs' catalyst / CH₂Cl₂ / 6 h / 20 °C

6.1: 3.17 g / 0.4percent H₂SO₄ / dioxane / 2 h / Heating

7.1: NaIO₄; SiO₂ / CH₂Cl₂ / 1 h / 20 °C

7.2: 70 percent / NaBH₄ / methanol / 1 h / 20 °C

8.1: 69 percent / benzene / 4 h / Heating

9.1: 54 percent / Pd(PPh₃)4 / dimethylsulfoxide; tetrahydrofuran / 2 h / 45 °C

With dmap; sodium periodate; silica gel; sodium hydride; triethylamine; sodium iodide; Grubbs catalyst first generation; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; butanone; benzene;

DOI:10.1021/jo010718c

upstream raw materials:

adenine

(1S,2R)-5-(4-methoxyphenylmethoxy)-1,3-dioxabicyclo[4.3.0]non-7-en-2-one

p-Methoxybenzyl bromide

3-C-allyl-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

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