2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

Base Information

Chemical Name:2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine
CAS No.:845254-27-5
Molecular Formula:C₅₆H₈₉N₉O₈Si₄
Molecular Weight:1128.72
Hs Code.:

Synonyms:2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

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Chemical Property of 2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

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Technology Process of 2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

There total 7 articles about 2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine 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: 71.8%

: 845254-26-4
2'-O-(tert-butyldimethylethylsilyl)-6-O-benzylacycloguanosine

: 845254-25-3
5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzyl-2-bromoguanosine

: 845254-27-5
2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

Guidance literature:: With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 20 - 90 ℃; for 16.5h;
DOI:10.1021/ja045108j

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 845254-27-5
2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / imidazole / dimethylformamide

2: 64 percent / diethylazodicarboxylate; Ph₃P / dioxane / 2 h

3: 61.7 percent / SbBr₃; t-BuNO₂; CH₂Br₂ / toluene / 1 h / -10 °C

4: 71.8 percent / Cs₂CO₃; Pd(OAc)2; BINAP / toluene / 16.5 h / 20 - 90 °C

With 1H-imidazole; palladium diacetate; 2-Methyl-2-nitropropane; antimony(III) bromide; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; diethylazodicarboxylate; 1,1-dibromomethane; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja045108j

Reference yield:

: 59277-89-3
acycloguanosine

: 845254-27-5
2-N-[2-(2'-O-tert-butyldimethylethylsilyl-6-O-benzylacycloinosyl)]-5'-O,3'-O,2'-O-tris(tert-butyldimethylethylsilyl)-6-O-benzylguanosine

Guidance literature:: Multi-step reaction with 3 steps

1: 87 percent / imidazole / dimethylformamide / 20 °C

2: 60 percent / diethylazodicarboxylate; Ph₃P / dioxane

3: 71.8 percent / Cs₂CO₃; Pd(OAc)2; BINAP / toluene / 16.5 h / 20 - 90 °C

With 1H-imidazole; palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja045108j