6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Base Information

Chemical Name:6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]
CAS No.:439097-85-5
Molecular Formula:C₅₉H₆₀N₇O₉P
Molecular Weight:1042.14
Hs Code.:

Synonyms:6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

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Chemical Property of 6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

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Technology Process of 6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

There total 4 articles about 6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate] 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: 29.0%

: 82935-40-8
(S)-(-)-1-trityl-2-pyrrolidinecarboxamide

: 439097-84-4
6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-(methyl N,N-diisopropylphosphoramidite)

: 439097-85-5
6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Guidance literature:: (S)-(-)-1-trityl-2-pyrrolidinecarboxamide; 6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-(methyl N,N-diisopropylphosphoramidite); With 5-(3,5-dinitrophenyl)-1H-tetrazole; In acetonitrile; at 20 ℃; for 0.166667h;

With tert.-butylhydroperoxide; In acetonitrile; at 20 ℃; for 5h;

With iodine; In pyridine; water; at 20 ℃; for 0.5h; Further stages.;
DOI:10.1021/jo016176g

Reference yield:

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 439097-85-5
6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Guidance literature:: Multi-step reaction with 3 steps

1.1: chlorotrimethylsilane / pyridine / 0.5 h / 20 °C

1.2: pyridine / 1 h / 20 °C

1.3: 90 percent / conc. NH₃ / pyridine / 0.5 h / 20 °C

2.1: 85 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 2 h / 20 °C

3.1: 5-(3,5-dinitrophenyl)-1H-tetrazole / acetonitrile / 0.17 h / 20 °C

3.2: tert-BuOOH / acetonitrile / 5 h / 20 °C

3.3: 29 percent / I₂ / pyridine; H₂O / 0.5 h / 20 °C

With chloro-trimethyl-silane; N,N-diisopropylamine tetrazolide; 5-(3,5-dinitrophenyl)-1H-tetrazole; In pyridine; dichloromethane; acetonitrile;
DOI:10.1021/jo016176g

Reference yield:

: 362-75-4
2',3'-isopropylidene adenosine

: 439097-85-5
6-N-(4,4'-dimethoxytrityl)-2',3'-O-isopropylideneadenosine 5'-[methyl N-(N-trityl-L-prolyl)phosphoramidate]

Guidance literature:: Multi-step reaction with 3 steps

1.1: chlorotrimethylsilane / pyridine / 0.5 h / 20 °C

1.2: pyridine / 1 h / 20 °C

1.3: 90 percent / conc. NH₃ / pyridine / 0.5 h / 20 °C

2.1: 85 percent / diisopropylammonium tetrazolide / CH₂Cl₂ / 2 h / 20 °C

3.1: 5-(3,5-dinitrophenyl)-1H-tetrazole / acetonitrile / 0.17 h / 20 °C

3.2: tert-BuOOH / acetonitrile / 5 h / 20 °C

3.3: 29 percent / I₂ / pyridine; H₂O / 0.5 h / 20 °C

With chloro-trimethyl-silane; N,N-diisopropylamine tetrazolide; 5-(3,5-dinitrophenyl)-1H-tetrazole; In pyridine; dichloromethane; acetonitrile;
DOI:10.1021/jo016176g