1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

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Chemical Name:1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil
CAS No.:1361928-14-4
Molecular Formula:C₄₃H₅₁F₃N₅O₁₀P
Molecular Weight:885.874
Hs Code.:

1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

Synonyms:1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

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Chemical Property of 1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

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Technology Process of 1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

There total 10 articles about 1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil 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: 70.0%

: 1361928-13-3
1-[2'-O-methyl-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl]uracil

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1361928-14-4
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1.25h;
DOI:10.1021/jo202666m

Reference yield:

: 1361928-12-2
1-(2'-O-methyl-4'-C-trifluoroacetylaminomethyl-β-D-ribofuranosyl)uracil

: 1361928-14-4
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

Guidance literature:: Multi-step reaction with 2 steps

1: pyridine / 24 h / 20 °C

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.25 h / 20 °C

With N-ethyl-N,N-diisopropylamine; In pyridine; dichloromethane;
DOI:10.1021/jo202666m

Reference yield:

: 1361928-06-4
1-(2'-O-acetyl-3',5'-di-O-benzyl-4'-C-azidomethyl-β-D-ribofuranosyl)-3-(4-methoxybenzyl)uracil

: 1361928-14-4
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}uracil

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium methylate / methanol / 3 h / 20 °C

2.1: sodium hydride / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

3.1: ammonium cerium (IV) nitrate / water; acetonitrile / 55 h / 20 °C

4.1: water; triphenylphosphine / tetrahydrofuran / 4 h / 45 °C

5.1: triethylamine / tetrahydrofuran / 0 - 20 °C

6.1: palladium 10% on activated carbon; hydrogen / ethanol / 16 h / 70 °C

7.1: pyridine / 24 h / 20 °C

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.25 h / 20 °C

With ammonium cerium (IV) nitrate; palladium 10% on activated carbon; water; hydrogen; sodium methylate; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo202666m