N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Base Information

• Chemical Name: N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS No.: 253270-07-4
• Molecular Formula: C₃₆H₅₂N₆O₆Si₂
• Molecular Weight: 721.016

Synonyms:N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property of N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property:

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Technology Process of N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

There total 1 articles about N²-(2-nitro-3-methylphenyl)-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine 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: 93.0%

O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (236427-57-9) + trifluoromethanesulphonic acid (2-nitro-3-methylphenyl ester) (145209-21-8) → N2-(2-nitro-3-methylphenyl)-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (253270-07-4)

Guidance literature:

With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 80 ℃; for 16h;

DOI:10.1021/ja991328z

Reference yield:

N2-(2-nitro-3-methylphenyl)-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (253270-07-4) → 2-(2-amino-3-methyl-phenylamino)-9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-1,9-dihydro-purin-6-one

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; ethyl acetate; for 16h; under 2585.74 Torr;

DOI:10.1021/ja991328z

Reference yield:

N2-(2-nitro-3-methylphenyl)-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (253270-07-4) → N2-(2-acetylamino-3-methylphenyl)-2'-deoxyguanosine

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10 percent Pd/C / ethyl acetate; ethanol / 16 h / 2585.74 Torr

2: CH₂Cl₂ / 16 h / 20 °C

3: 95 percent / Bu₄NF / tetrahydrofuran / 1 h / 20 °C

With tetrabutyl ammonium fluoride; hydrogen; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; ethyl acetate; 1: Catalytic hydrogenation / 2: Acetylation / 3: deprotection;

DOI:10.1021/ja991328z

upstream raw materials:

O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

trifluoromethanesulphonic acid (2-nitro-3-methylphenyl ester)

Downstream raw materials:

N²-(2-acetylamino-3-methylphenyl)-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

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