8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

Base Information

• Chemical Name: 8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS No.: 479408-32-7
• Molecular Formula: C₄₅H₅₆N₆O₄Si₂
• Molecular Weight: 801.148

Synonyms:8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property of 8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

There total 12 articles about 8-(N-2-amino-pyrene)-O⁶-benzyl-3',5'-O-bis(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: 90.0%

8-(N2-aminopyrene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N2-dimethoxytrityl-2'-deoxyguanosine (479408-27-0) → 8-(N-2-amino-pyrene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-32-7)

Guidance literature:

With hydrogenchloride; In methanol;

DOI:10.1080/15257770902736426

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 8-(N-2-amino-pyrene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-32-7)

Guidance literature:

Multi-step reaction with 3 steps

1: imidazole / dimethylformamide

2: 87 percent / KO-t-Bu; XANTPHOS / Pd₂dba3 / toluene / 2 h / 100 °C

3: ZnBr₂ / CH₂Cl₂; propan-2-ol

With 1H-imidazole; potassium tert-butylate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; zinc dibromide; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1016/S0040-4039(03)01484-9

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → 8-(N-2-amino-pyrene)-O6-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-32-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide; tetrahydrofuran / 5 h / 20 °C

2: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / dioxane / 5 h / 20 °C

3: 94 percent / pyridine / 20 °C

4: 51 percent / sodium tert-butoxide; rac-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / Pd₂(dba)3 / toluene / 100 °C / Heating

5: 84 percent / HCl / methanol / 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; sodium t-butanolate; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; toluene; 4: Buchwald-Hartwig coupling;

DOI:10.1021/ol026474f

upstream raw materials:

8-(N₂-aminopyrene)-O₆-benzyl-3',5'-O-bis(tert-butyldimethylsilyl)-N₂-dimethoxytrityl-2'-deoxyguanosine

1-bromopyrene

tert-butyldimethylsilyl chloride

(2R,3S,5R)-5-(8-Amino-6-benzyloxy-2-{[bis-(4-methoxy-phenyl)-phenyl-methyl]-amino}-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-ol

Downstream raw materials:

C₃₃H₂₈N₆O₄

N-(deoxyguanosin-8-yl)-1-aminopyrene

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