((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

Base Information

• Chemical Name: ((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
• CAS No.: 1449328-99-7
• Molecular Formula: C₃₅H₄₄N₈O₇Si
• Molecular Weight: 716.869
• Mol file: 1449328-99-7.mol

Synonyms:((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

Chemical Property of ((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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((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

There total 6 articles about ((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 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:

(3aR,6R,6aS)-6-(2-azido-6-(dibocamino)-9H-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole-4-carbaldehyde (1449328-98-6) + (4-bromophenyl)(trimethylsilyl)acetylene (16116-78-2) → ((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:

(4-bromophenyl)(trimethylsilyl)acetylene; With magnesium; In tetrahydrofuran; at 50 ℃; for 0.5h; Inert atmosphere;

With iodine; In tetrahydrofuran; at 50 ℃; for 3h; Inert atmosphere;

(3aR,6R,6aS)-6-(2-azido-6-(dibocamino)-9H-purin-9-yl)-2,2-dimethyl-6,6a-dihydro-3aH-cyclopenta[d][1,3]dioxole-4-carbaldehyde; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/asia.201300303

Reference yield:

2-Amino-6-chloropurin (10310-21-1) → ((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 8 steps

1.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 18 h / 50 °C / Inert atmosphere

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

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

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

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

6.1: 2,2-dimethoxy-propane; toluene-4-sulfonic acid / acetone / 18 h / 20 °C

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

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

8.2: 3 h / 50 °C / Inert atmosphere

8.3: 18 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; sodium azide; diiodomethane; n-Butyl nitrite; di-isopropyl azodicarboxylate; ammonia; Dess-Martin periodane; toluene-4-sulfonic acid; magnesium; N,N-dimethylethylenediamine; triphenylphosphine; 2,2-dimethoxy-propane; In tetrahydrofuran; ethanol; dichloromethane; water; acetone; acetonitrile; 1.1: |Mitsunobu Displacement / 7.1: |Dess-Martin Oxidation / 8.1: |Grignard Reaction / 8.2: |Grignard Reaction / 8.3: |Grignard Reaction;

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

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

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

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-ethynylphenyl)methanol