((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

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-ethynylphenyl)methanol
CAS No.:1449329-00-3
Molecular Formula:C₃₂H₃₆N₈O₇
Molecular Weight:644.687
Hs Code.:

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-ethynylphenyl)methanol

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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-ethynylphenyl)methanol

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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-ethynylphenyl)methanol

There total 7 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-ethynylphenyl)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: 69.0%

: 1449328-99-7
((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

: 1449329-00-3
((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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1002/asia.201300303

Reference yield:

: 10310-21-1
2-Amino-6-chloropurin

: 1449329-00-3
((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

Guidance literature:: Multi-step reaction with 9 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

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; sodium azide; diiodomethane; n-Butyl nitrite; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; 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:

: 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)-9H-purin-2-amine

: 1449329-00-3
((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

Guidance literature:: Multi-step reaction with 8 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

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With dmap; copper(l) iodide; sodium azide; diiodomethane; n-Butyl nitrite; tetrabutyl ammonium fluoride; 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