6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

Base Information

Chemical Name:6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]
CAS No.:297731-15-8
Molecular Formula:C₃₇H₄₉N₆O₉PSi
Molecular Weight:780.89
Hs Code.:

Synonyms:6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

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Chemical Property of 6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

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Technology Process of 6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

There total 5 articles about 6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite] 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: 86.0%

: 149578-28-9
2-(trimethylsilyl)ethyl N,N,N',N'-tetraisopropyl phosphorodiamidite

: 297731-14-7
6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine

: 297731-15-8
6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

Guidance literature:: With N,N-diisopropylamine tetrazolide; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/jo016176g

Reference yield:

: 3868-35-7
6-N-acetyl-8-oxoadenosine

: 297731-15-8
6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

Guidance literature:: Multi-step reaction with 4 steps

1: 92 percent / pyridine / 12 h / 20 °C

2: 87 percent / 4-(N,N-dimethylamino)pyridine / pyridine / 3 h / 20 °C

3: 93 percent / tetrabutylammonium fluoride; AcOH / tetrahydrofuran / 7 h / 20 °C

4: 86 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; acetic acid; In tetrahydrofuran; pyridine; dichloromethane;
DOI:10.1021/jo016176g

Reference yield:

: 2946-39-6
8-bromoadenosine

: 297731-15-8
6-N-acetyl-2',3'-di-O-benzoyl-8-oxoadenosine 5'-[2-(trimethylsilyl)ethyl N,N-diisopropylphosphoramidite]

Guidance literature:: Multi-step reaction with 7 steps

2: NaOAc; AcOH / 3 h / 120 °C

3: NH₃*pyridine / 6 h / 20 °C

4: 94 percent / pyridine / 12 h / 20 °C

5: 88 percent / DMAP; pyridine / 4 h / 20 °C

6: 93 percent / TBAF*H₂O; AcOH / tetrahydrofuran / 12 h / 20 °C

7: 81 percent / diisopropylammonium terazolide / CH₂Cl₂ / 1.5 h / 20 °C

With pyridine; dmap; pyridine amine; N,N-diisopropylamine tetrazolide; tetrabutyl ammonium fluoride; sodium acetate; acetic acid; In tetrahydrofuran; dichloromethane; 1: Hydrolysis / 2: Acetylation / 3: Deacetylation / 4: Etherification / 5: Acylation / 6: Hydrolysis / 7: Condensation;
DOI:10.1016/S0040-4039(00)00926-6