3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine

Base Information

• Chemical Name: 3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine
• CAS No.: 190506-33-3
• Molecular Formula: C₃₀H₄₆FN₅O₆Si₂
• Molecular Weight: 647.895
• Mol file: 190506-33-3.mol

Synonyms:3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine

Chemical Property of 3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine

There total 7 articles about 3′,5′-O-bis(tert-butyldimethylsilyl)-O⁶-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine 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%

3'-O,5'-O-bis(tert-butyldimethylsilyl)-O6-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine (147299-48-7) → 3′,5′-O-bis(tert-butyldimethylsilyl)-O6-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine (190506-33-3)

Guidance literature:

With tert.-butylnitrite; poly[4-vinylpyridinium poly(hydrogen fluoride)]; In toluene; at -65 - -5 ℃;

DOI:10.1002/1521-3765(20001117)6:22<4188::AID-CHEM4188>3.0.CO;2-N

Reference yield: 70.0%

3'-O,5'-O-bis(tert-butyldimethylsilyl)-O6-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine (147299-48-7) → ((2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-2-yl)-methanol (190506-34-4) + 3′,5′-O-bis(tert-butyldimethylsilyl)-O6-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine (190506-33-3)

Guidance literature:

With tert.-butylnitrite; polyvinylpyridinium polyhydrogenfluoride; In toluene; at -5 - 0 ℃; for 0.5h; Yield given;

DOI:10.1016/S0040-4039(97)00540-6

Reference yield:

2-(4-nitrophenyl)ethanol (100-27-6) → 3′,5′-O-bis(tert-butyldimethylsilyl)-O6-(p-nitrophenylethyl)-2′-deoxy-2-fluoroguanosine (190506-33-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / PPh₃; DEAD / dioxane / 24 h

2: 75 percent / poly[4-vinylpyridinium poly(hydrogen fluoride)]; t-BuONO / toluene / -65 - -5 °C

With tert.-butylnitrite; poly[4-vinylpyridinium poly(hydrogen fluoride)]; triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; toluene;

DOI:10.1002/1521-3765(20001117)6:22<4188::AID-CHEM4188>3.0.CO;2-N

upstream raw materials:

tert-butyldimethylsilyl chloride

((2R,3S,5R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-{2-fluoro-6-[2-(4-nitro-phenyl)-ethoxy]-purin-9-yl}-tetrahydro-furan-2-yl)-methanol

3'-O,5'-O-bis(tert-butyldimethylsilyl)-O⁶-(2''-(4'''-nitrophenyl)ethyl)-2'-deoxyguanosine

2-(4-nitrophenyl)ethanol

Downstream raw materials:

2-fluoro-O⁶-(2-(p-nitrophenyl)ethyl)-2'-deoxyinosine

4-{9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-ylamino}-butane-1,2-diol

{9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-(3-[2,2';5',2'']terthiophen-5-yl-propyl)-amine

{9-[4-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-(3-pyren-1-yl-propyl)-amine