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

Base Information

• Chemical Name: O⁶-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine
• CAS No.: 479408-22-5
• Molecular Formula: C₂₉H₄₆BrN₅O₄Si₂
• Molecular Weight: 664.79
• Mol file: 479408-22-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about O⁶-benzyl-8-bromo-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: 78.0%

benzyl alcohol (100-51-6,185532-71-2) + 3',5'-O,O'-bis(tert-butyldimethylsilyl)-8-bromo-2'-deoxyguanosine (479408-21-4) → O6-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-22-5)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane; at 20 ℃; for 5h;

DOI:10.1021/ol026474f

Reference yield:

8-bromo-2'-deoxyguanosine (13389-03-2) → O6-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-22-5)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole; pyridine / 1 h

2: PPh₃; DIAD / dioxane / 1 h / 20 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In 1,4-dioxane;

DOI:10.1081/NCN-200060267

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → O6-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-22-5)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With 1H-imidazole; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide;

DOI:10.1021/ol026474f

upstream raw materials:

benzyl alcohol

3',5'-O,O'-bis(tert-butyldimethylsilyl)-8-bromo-2'-deoxyguanosine

tert-butyldimethylsilyl chloride

8-bromo-2'-deoxyguanosine

Downstream raw materials:

N²-iso-butyryl-O⁶-benzyl-8-bromo-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine

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

O₆-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

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

Refernces

• 1、 Boege,Szombati,Meier. "Synthesis of DNA-oligonucleotides damaged by arylamine-modified 2′-deoxyguanosine". . p. 705 - 708. Retrieved 2008/09/17.
• 2、 Gillet, Ludovic C. J.,Schaerer, Orlando D.. "Preparation of C8-amine and acetylamine adducts of 2′-deoxyguanosine suitably protected for DNA synthesis". . p. 4205 - 4208. Retrieved 2007/10/03.