(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

Base Information

• Chemical Name: (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
• CAS No.: 455330-13-9
• Molecular Formula: C₃₀H₄₃N₅O₅Si₂
• Molecular Weight: 609.873

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

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Technology Process of (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

There total 4 articles about (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 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: 58.0%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + N-benzoyladenine (4005-49-6) + (1R,5S,7S,11R)-11-{[tert-butyl(dimethyl)silyl]oxy}-3-ethoxy-2,8-dioxatricyclo[5.3.1.01,5]undecan-5-ol → N-{9-[11-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-2,8-dioxa-tricyclo[5.3.1.01,5]undec-3-yl]-9H-purin-6-yl}-benzamide + (1R,3R,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 + (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)

Guidance literature:

N-benzoyladenine; With benzenesulfonamide; In 1,2-dichloro-ethane; at 80 ℃; for 2h;

trimethylsilyl trifluoromethanesulfonate; (1R,5S,7S,11R)-11-{[tert-butyl(dimethyl)silyl]oxy}-3-ethoxy-2,8-dioxatricyclo[5.3.1.0^1,5]undecan-5-ol; In 1,2-dichloro-ethane; at 80 ℃; for 7h;

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-[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)

Guidance literature:

Multi-step reaction with 3 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

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

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-[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)

Guidance literature:

Multi-step reaction with 4 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

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

DOI:10.1055/s-2002-25755

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

N-benzoyladenine

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

(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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