(3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

Base Information

• Chemical Name: (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide
• CAS No.: 167297-07-6
• Molecular Formula: C₃₆H₄₆N₈O₄
• Molecular Weight: 654.812

Synonyms:

Chemical Property of (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

There total 15 articles about (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide 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:

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine (16321-99-6) → (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide (167297-07-6)

Guidance literature:

Multi-step reaction with 8 steps

1: t-BuONO; pyridine*HCl; CuCl / CH₂Cl₂ / 0 - 20 °C

2: i-Pr₂NEt / propan-2-ol / Heating

3: aq. Na₂CO₃ / methanol

4: acetone

5: KMnO₄; KOH / dioxane

6: SOCl₂ / Heating

7: CH₂Cl₂

8: dimethylsulfoxide / 120 °C

With potassium hydroxide; potassium permanganate; thionyl chloride; tert.-butylnitrite; pyridine hydrochloride; sodium carbonate; N-ethyl-N,N-diisopropylamine; copper(l) chloride; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; acetone; 1: Diazotization / 2: Substitution / 3: Deacetylation / 4: Condensation / 5: Oxidation / 6: Chlorination / 7: Acylation / 8: Substitution;

DOI:10.1016/S0960-894X(00)00017-2

Reference yield:

(2R,3R,4R,5R)-4-(acetyloxy)-2-[(acetyloxy)methyl]-5-(2,6-dichloro-9H-purin-9-yl)tetrahydro-3-furanyl acetate (3056-18-6) → (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide (167297-07-6)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt / propan-2-ol / Heating

2: aq. Na₂CO₃ / methanol

3: acetone

4: KMnO₄; KOH / dioxane

5: SOCl₂ / Heating

6: CH₂Cl₂

7: dimethylsulfoxide / 120 °C

With potassium hydroxide; potassium permanganate; thionyl chloride; sodium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; acetone; 1: Substitution / 2: Deacetylation / 3: Condensation / 4: Oxidation / 5: Chlorination / 6: Acylation / 7: Substitution;

DOI:10.1016/S0960-894X(00)00017-2

Reference yield:

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate (15373-23-6,339091-08-6) → (3aS,4S,6R,6aR)-6-[6-(2,2-Diphenyl-ethylamino)-2-(2-piperidin-1-yl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide (167297-07-6)

Guidance literature:

Multi-step reaction with 7 steps

1: i-Pr₂NEt / propan-2-ol / Heating

2: K₂CO₃ / methanol

3: acetone

4: KMnO₄; KOH / dioxane

5: SOCl₂ / Heating

6: CH₂Cl₂

7: dimethylsulfoxide / 120 °C

With potassium hydroxide; potassium permanganate; thionyl chloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; methanol; dichloromethane; dimethyl sulfoxide; isopropyl alcohol; acetone; 1: Substitution / 2: debenzoylation / 3: Condensation / 4: Oxidation / 5: Chlorination / 6: Acylation / 7: Substitution;

DOI:10.1016/S0960-894X(00)00017-2

upstream raw materials:

1-(2-aminoethyl)piperidine

(3aS,4S,6R,6aR)-6-[2-Chloro-6-(2,2-diphenyl-ethylamino)-purin-9-yl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxole-4-carboxylic acid ethylamide

(2R,3R,4R,5R)-2-((benzoyloxy)methyl)-5-(2,6-dichloro-9H-purin-9-yl)tetrahydrofuran-3,4-diyl dibenzoate

2-amino-6-chloro-9-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)purine

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