6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine

Base Information

• Chemical Name: 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine
• CAS No.: 1449328-92-0
• Molecular Formula: C₃₃H₃₀ClN₅O₃
• Molecular Weight: 580.086
• Mol file: 1449328-92-0.mol

Synonyms:6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine

Chemical Property of 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine

There total 1 articles about 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine 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: 95.0%

2-Amino-6-chloropurin (10310-21-1) + (3aS,4S,6aR)-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-ol (163226-45-7) → 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine (1449328-92-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 50 ℃; for 18h; Inert atmosphere;

DOI:10.1002/asia.201300303

Reference yield: 80.0%

6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine (1449328-92-0) → 6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-2-iodo-9H-purine (1449328-93-1)

Guidance literature:

With copper(l) iodide; diiodomethane; n-Butyl nitrite; In acetonitrile; at 0 - 50 ℃; for 3h; Inert atmosphere;

DOI:10.1002/asia.201300303

Reference yield:

6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-9H-purin-2-amine (1449328-92-0) → ((3aR,6R,6aS)-6-(2-azido-6-(dibocamino)-9H-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)(4-((trimethylsilyl)ethynyl)phenyl)methanol (1449328-99-7)

Guidance literature:

Multi-step reaction with 7 steps

1.1: copper(l) iodide; diiodomethane; n-Butyl nitrite / acetonitrile / 3 h / 0 - 50 °C / Inert atmosphere

2.1: ammonia / tetrahydrofuran / 6 h / 50 °C / Sealed tube

3.1: copper(l) iodide; N,N-dimethylethylenediamine; sodium azide / water; ethanol / 1.5 h / 90 °C / Microwave irradiation

4.1: dmap / dichloromethane / 4 h / 20 °C

5.1: 2,2-dimethoxy-propane; toluene-4-sulfonic acid / acetone / 18 h / 20 °C

6.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

7.1: magnesium / tetrahydrofuran / 0.5 h / 50 °C / Inert atmosphere

7.2: 3 h / 50 °C / Inert atmosphere

7.3: 18 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; sodium azide; diiodomethane; n-Butyl nitrite; ammonia; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; N,N-dimethylethylenediamine; 2,2-dimethoxy-propane; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; acetonitrile; 6.1: |Dess-Martin Oxidation / 7.1: |Grignard Reaction / 7.2: |Grignard Reaction / 7.3: |Grignard Reaction;

DOI:10.1002/asia.201300303

upstream raw materials:

2-Amino-6-chloropurin

(3aS,4S,6aR)-2,2-dimethyl-6-[(triphenylmethoxy)methyl]-2H,3aH,4H,6aH-cyclopenta[d][1,3]dioxol-4-ol

Downstream raw materials:

((3aR,6R,6aS)-6-(2-azido-6-(dibocamino)-9H-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)(4-((trimethylsilyl)ethynyl)phenyl)methanol

((3aR,6R,6aS)-6-(2-azido-6-(dibocamino)-9H-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)(4-ethynylphenyl)methanol

6-chloro-9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-2-iodo-9H-purine

9-((3aS,4R,6aR)-2,2-dimethyl-6-((trityloxy)methyl)-4,6a-dihydro-3aH-cyclopenta[d][1,3]dioxol-4-yl)-2-iodo-9H-purin-6-amine