5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Base Information

• Chemical Name: 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine
• CAS No.: 1449294-99-8
• Molecular Formula: C₃₅H₅₂N₆O₁₁SSi
• Molecular Weight: 792.983

Synonyms:5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property of 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]guanosine

There total 9 articles about 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O⁶-[2-(4-nitrophenyl)ethyl]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: 87.0%

5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-8-(hydroxymethyl)-N2-isobutyryl-2’,3’-O-isopropylidene-O6-[2-(4-nitrophenyl)ethyl]guanosine (1449294-98-7) + methanesulfonyl chloride (124-63-0) → 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (1449294-99-8)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;

DOI:10.1002/hlca.201300043

Reference yield:

2',3'-isopropylideneguanosine (362-76-5) → 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (1449294-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 26 °C

2.1: dmap / pyridine / 13 h / 23 - 80 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 - 24 °C

3.2: 2 h / -78 - 24 °C

4.1: sodium tetrahydroborate / ethanol / 0.5 h

5.1: 1,4-dioxane / 1.5 h

6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 2 h

7.1: acetic acid / water / 1 h

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 6.1: |Mitsunobu Displacement;

DOI:10.1002/hlca.201300043

Reference yield:

chlorodimethyl(1,1,2-trimethylpropyl)silane (67373-56-2) → 5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylidene-8-{[(methylsulfonyl)oxy]methyl}-O6-[2-(4-nitrophenyl)ethyl]guanosine (1449294-99-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 26 °C

2.1: dmap / pyridine / 13 h / 23 - 80 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 1 h / -78 - 24 °C

3.2: 2 h / -78 - 24 °C

4.1: sodium tetrahydroborate / ethanol / 0.5 h

5.1: 1,4-dioxane / 1.5 h

6.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 2 h

7.1: acetic acid / water / 1 h

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C

With 1H-imidazole; dmap; sodium tetrahydroborate; di-isopropyl azodicarboxylate; acetic acid; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,4-dioxane; pyridine; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; 6.1: |Mitsunobu Displacement;

DOI:10.1002/hlca.201300043

upstream raw materials:

5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-2’,3’-O-isopropylideneguanosine

2',3'-isopropylideneguanosine

chlorodimethyl(1,1,2-trimethylpropyl)silane

5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N2-isobutyryl-2’,3’-O-isopropylideneguanosine

Downstream raw materials:

5’-O-[dimethyl(1,1,2-trimethylpropyl)silyl]-N²-isobutyryl-2’,3’-O-isopropylidene-O⁶-[2-(4-nitrophenyl)ethyl]guanosine-8-methyl-(815’-S)-N4-benzoyl-2’,3’-O-isopropylidene-6-{[ (4-methoxyphenyl)diphenylmethoxy]methyl}-5’-thiocytidine

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