5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine

Base Information

• Chemical Name: 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine
• CAS No.: 195375-54-3
• Molecular Formula: C₃₉H₄₈N₆O₄Si
• Molecular Weight: 692.933
• Mol file: 195375-54-3.mol

Synonyms:5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine

Chemical Property of 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine

There total 9 articles about 5'-O-(tert-butyldimethylsilyl)-N²-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine 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%

C35H42N6O3Si (1417713-28-0) + isobutyryl chloride (79-30-1) → 5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine (195375-54-3)

Guidance literature:

C₃₅H₄₂N₆O₃Si; With triethylamine; In pyridine; for 0.25h;

isobutyryl chloride; In pyridine; for 1h;

DOI:10.1016/j.tet.2012.11.028

Reference yield:

3'-amino-2',3'-dideoxyaguanosine (66323-49-7) → 5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine (195375-54-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / N,N-dimethyl-formamide / 0.5 h / 60 °C

1.2: 3 h / 20 °C

2.1: N,N-dimethyl-formamide / 20 °C

3.1: triethylamine / pyridine / 0.25 h

3.2: 1 h

With triethylamine; In pyridine; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2012.11.028

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 5'-O-(tert-butyldimethylsilyl)-N2-isobutyryl-3'-tritylamino-2',3'-dideoxyguanosine (195375-54-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) Et₃N, DMAP, 2.) 2 M NaOH / 1.) DMF, room temperature, 2 h, 2.) MeOH, dioxane, 0 deg C, 15 min

2: LiN₃, PPh₃, DEAD / dimethylformamide / 5 h / Ambient temperature

3: 60 percent / H₂ / 10percent Pd/C / ethanol

4: 43.8 g / Et₃N / pyridine / 16 h / Ambient temperature

With dmap; sodium hydroxide; lithium azide; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In pyridine; ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jo970801t

upstream raw materials:

trityl chloride

N-{9-[(2R,4S,5S)-4-Amino-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-6-oxo-6,9-dihydro-1H-purin-2-yl}-isobutyramide

tert-butyldimethylsilyl chloride

[(2R,3R,5R)-2-(hydroxymethyl)-5-[2-(2-methylpropanoylamino)-6-oxo-1H-purin-9-yl]tetrahydrofuran-3-yl] benzoate

Downstream raw materials:

Diphenyl-carbamic acid 9-[(2R,4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-isobutyrylamino-9H-purin-6-yl ester

Diphenyl-carbamic acid 9-[(2R,4S,5S)-5-hydroxymethyl-4-(trityl-amino)-tetrahydro-furan-2-yl]-2-isobutyrylamino-9H-purin-6-yl ester

N²-isobutyryl-3'-NH-trityl-2',3'-dideoxyguanosine

Refernces

• 1、 -. "Synthesis of protected 3'-amino nucleoside monomers". Page/Page column 7; sheet 2. . Retrieved 2008/06/13.