9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine

Base Information

• Chemical Name: 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine
• CAS No.: 184167-15-5
• Molecular Formula: C₄₇H₅₇N₅O₆Si
• Molecular Weight: 816.085
• Mol file: 184167-15-5.mol

Synonyms:

Chemical Property of 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine

There total 6 articles about 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine 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: 45.0%

dihydropyran (3174-74-1) + 5-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-7-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-hept-3-yn-1-ol (184167-12-2) → 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine (184167-15-5)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane;

DOI:10.1016/0968-0896(96)00139-3

Reference yield:

benzoyltrimethylsilane (5908-41-8) → 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine (184167-15-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) M LDA, 2.) CuCN, LiCl, 3.) ZnI₂, Simmons-Smith reagent

2: 81 percent / conc. aq. NH₃ / methanol / 18 h

3: 82 percent / KOBut / tetrahydrofuran / 1.75 h / 0 °C

4: 45 percent / PPTS / CH₂Cl₂

With ammonium hydroxide; potassium tert-butylate; pyridinium p-toluenesulfonate; (iodomethyl)zinc iodide; lithium chloride; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0968-0896(96)00139-3

Reference yield:

9-((3aR,4R,6R,6aR)-6-{2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-but-3-ynyl}-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-9H-purin-6-ylamine → 9-{(3aR,4R,6R,6aR)-6-[2-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-6-phenyl-6-(tetrahydro-pyran-4-yloxy)-hex-3-ynyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl}-9H-purin-6-ylamine (184167-15-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 84 percent / pyridine / 7 h / Ambient temperature

2: 1.) M LDA, 2.) CuCN, LiCl, 3.) ZnI₂, Simmons-Smith reagent

3: 81 percent / conc. aq. NH₃ / methanol / 18 h

4: 82 percent / KOBut / tetrahydrofuran / 1.75 h / 0 °C

5: 45 percent / PPTS / CH₂Cl₂

With pyridine; ammonium hydroxide; potassium tert-butylate; pyridinium p-toluenesulfonate; (iodomethyl)zinc iodide; lithium chloride; zinc(II) iodide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/0968-0896(96)00139-3

upstream raw materials:

dihydropyran

5-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-7-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-hept-3-yn-1-ol

benzoyltrimethylsilane

5-[(3aR,4R,6R,6aR)-6-(6-Amino-purin-9-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-ylmethyl]-7-(tert-butyl-diphenyl-silanyloxy)-1-phenyl-1-trimethylsilanyl-hept-3-yn-1-ol

Downstream raw materials:

5'-deoxy-5'-[1-phenyl-1-(4-tetrahydropyranyloxy)-7-hydroxy-3-heptyn-5-yl]2',3'-O-isopropylideneadenosine