N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine

Base Information

• Chemical Name: N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine
• CAS No.: 444594-35-8
• Molecular Formula: C₄₀H₆₀N₆O₅Si₂
• Molecular Weight: 761.125
• Mol file: 444594-35-8.mol

Synonyms:N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine

Chemical Property of N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine

There total 5 articles about N²-isobutyryl-O⁶-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine 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: 75.0%

p-toluidine (106-49-0,12221-03-3) + N2-iso-butyryl-O6-benzyl-8-bromo-3',5'-bis-O-(tert-butyldimethylsilyl)-2'-deoxyguanosine (444594-32-5) → N2-isobutyryl-O6-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine (444594-35-8)

Guidance literature:

With 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,2-dimethoxyethane; at 80 ℃; for 50h;

DOI:10.1055/s-2002-25354

Reference yield:

O6-benzyl-8-bromo-3',5'-O-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine (479408-22-5) → N2-isobutyryl-O6-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine (444594-35-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / pyridine / 1 h / 20 °C

2: 75 percent / K₃PO₄; tris(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl / 1,2-dimethoxy-ethane / 50 h / 80 °C

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In pyridine; 1,2-dimethoxyethane;

DOI:10.1021/jo061803t

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → N2-isobutyryl-O6-benzyl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxy-guanosine (444594-35-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 83 percent / imidazole; pyridine / 1 h / 20 °C

2: 72 percent / PPh₃; DIAD / dioxane / 1 h / 20 °C

3: 96 percent / pyridine / 1 h / 20 °C

4: 75 percent / rac-BINAP; K₂PO₄ / Pd₂(dba)3 / 1,2-dimethoxy-ethane / 50 h / 80 °C

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; triphenylphosphine; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In 1,4-dioxane; 1,2-dimethoxyethane;

DOI:10.1055/s-2002-25354

upstream raw materials:

p-toluidine

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

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

N²-isobutyryl-8N-(4-methylphenylamino)-3',5'-bis(tert-butyldimethylsilyl)-2'-deoxyguanosine

N²-isobutyryl-8N-(4-methylphenylamino)-2'-deoxyguanosine

N-(9-{5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-6-oxo-8-p-tolylamino-6,9-dihydro-1H-purin-2-yl)-isobutyramide

N-[6-hydroxy-9-(4-hydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolylamino-9H-purin-2-yl]-isobutyramide