(1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide

Base Information

• Chemical Name: (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide
• CAS No.: 455330-15-1
• Molecular Formula: C₂₁H₂₁N₅O₅
• Molecular Weight: 423.428

Synonyms:(1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide

Chemical Property of (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide

There total 5 articles about (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl)-9H-purin-6-yl]benzamide 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: 67.0%

(1R,3S,5S,7S,11R)-N-{[9-[11-(tert-butyl{dimethyl}silyl)oxy]-5-trimethylsilyloxy-2,8-dioxatricyclo[5.3.1.01,5]undec-3-yl]-9H-purin-6-yl}benzamide (455330-13-9) → (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.01,5]undec-3-yl)-9H-purin-6-yl]benzamide (455330-15-1)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 40 ℃; for 4h;

DOI:10.1055/s-2002-25755

Reference yield:

(1S,5S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-2-oxa-bicyclo[3.2.1]octane-5,6-diol → (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.01,5]undec-3-yl)-9H-purin-6-yl]benzamide (455330-15-1)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 95 percent / 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂ / 0.5 h / 20 °C

2.1: 72 percent / N-iodosuccinimide / CH₂Cl₂ / 12 h / -78 °C

3.1: 55 percent / aq. Et₃B; air / hexane / 72 h / -20 °C

4.1: BSA / 1,2-dichloro-ethane / 2 h / 80 °C

4.2: 58 percent / 1,2-dichloro-ethane / 7 h / 80 °C

5.1: 67 percent / Bu₄NF*3H₂O / tetrahydrofuran / 4 h / 40 °C

With benzenesulfonamide; N-iodo-succinimide; air; triethyl borane; tetrabutyl ammonium fluoride; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane; 1.1: Dess-Martin oxidation;

DOI:10.1055/s-2002-25755

Reference yield:

(1S,5R,8R)-8-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-2-oxabicyclo[3.2.1]octan-6-one (455330-09-3) → (1R,3S,5S,7S,11R)-N-[9-(5,11-dihydroxy-2,8-dioxatricyclo[5.3.1.01,5]undec-3-yl)-9H-purin-6-yl]benzamide (455330-15-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 72 percent / N-iodosuccinimide / CH₂Cl₂ / 12 h / -78 °C

2.1: 55 percent / aq. Et₃B; air / hexane / 72 h / -20 °C

3.1: BSA / 1,2-dichloro-ethane / 2 h / 80 °C

3.2: 58 percent / 1,2-dichloro-ethane / 7 h / 80 °C

4.1: 67 percent / Bu₄NF*3H₂O / tetrahydrofuran / 4 h / 40 °C

With benzenesulfonamide; N-iodo-succinimide; air; triethyl borane; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane; dichloromethane; 1,2-dichloro-ethane;

DOI:10.1055/s-2002-25755

upstream raw materials:

(1R,3S,5S,7S,11R)-N-{[9-[11-(tert-butyl{dimethyl}silyl)oxy]-5-trimethylsilyloxy-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl]-9H-purin-6-yl}benzamide

(1S,5R,8R)-8-{[tert-butyl(dimethyl)silyl]oxy}-5-hydroxy-2-oxabicyclo[3.2.1]octan-6-one

(1S,5R,8R)-8-{[tert-butyl(dimethyl)silyl]oxy}-5-(1-ethoxy-2-iodoethoxy)-2-oxabicyclo[3.2.1]octan-6-one

Downstream raw materials:

(1R,3S,5S,7S,11R)-N-{9-[5-hydroxy-11-(9-phenyl-9H-xanthen-9-yloxy)-2,8-dioxatricyclo[5.3.1.0^1,5]undec-3-yl]-9H-purin-6-yl}benzamide

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