N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Base Information

• Chemical Name: N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS No.: 486420-73-9
• Molecular Formula: C₇₀H₇₃N₅O₁₀Si₂
• Molecular Weight: 1200.55

Synonyms:N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property of N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

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Technology Process of N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O⁶-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

There total 6 articles about N²-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-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: 73.0%

(+/-)-10β-amino-7α,8β,9α-tris(benzoyloxy)-7,8,9,10-tetrahydrobenzopyrene + 2-bromo-6-benzyloxy-9-[2-deoxy-3,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine (236427-58-0) → N2-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (486420-73-9)

Guidance literature:

With caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; palladium diacetate; In toluene; at 85 ℃; for 16h;

DOI:10.1021/jo070204z

Reference yield:

(+/-)-7β,8α-bisbenzoyloxy-9β,10β-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene → N2-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (486420-73-9)

Guidance literature:

Multi-step reaction with 4 steps

1: LiN₃ / dimethylformamide / 20 °C

2: 513 mg / triethylamine / dimethylformamide / 0.5 h / 20 °C

3: 72 percent / hydrogen / Lindlar catalyst / tetrahydrofuran; ethanol / 2.33 h / 20 °C / 760.05 Torr

4: 73 percent / Cs₂CO₃; (+/-)-BINAP / Pd(OAc)2 / toluene / 16 h / 85 °C

With lithium azide; hydrogen; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; palladium diacetate; Lindlar's catalyst; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo070204z

Reference yield:

C34H23N3O5 → N2-[10-(7,8,9-trisbenzoyloxy-7,8,9,10-tetrahydrobenzo[a]pyrenyl)]-O6-benzyl-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (486420-73-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 513 mg / triethylamine / dimethylformamide / 0.5 h / 20 °C

2: 72 percent / hydrogen / Lindlar catalyst / tetrahydrofuran; ethanol / 2.33 h / 20 °C / 760.05 Torr

3: 73 percent / Cs₂CO₃; (+/-)-BINAP / Pd(OAc)2 / toluene / 16 h / 85 °C

With hydrogen; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triethylamine; palladium diacetate; Lindlar's catalyst; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo070204z

upstream raw materials:

2-bromo-6-benzyloxy-9-[2-deoxy-3,5-bis(O-tert-butyldimethylsilyl)-β-D-erythro-pentofuranosyl]purine

(+/-)-trans-7,8-Dihydrobenzopyrene-7,8-diol dibenzoate

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