3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

Base Information

Chemical Name:3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine
CAS No.:1416133-45-3
Molecular Formula:C₄₃H₅₃N₄O₁₁P
Molecular Weight:832.888
Hs Code.:

Synonyms:3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

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Chemical Property of 3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

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Technology Process of 3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

There total 8 articles about 3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine 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: 77.0%

: 1416133-44-2
5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

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

: 1416133-45-3
3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 3h; Inert atmosphere;
DOI:10.1039/c2ob26712h

Reference yield:

: 1300589-65-4
3',5'-di-O-benzyl-4'-C-(tert-butyldiphenylsilyloxymethyl)-5-methyluridine

: 1416133-45-3
3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

Guidance literature:: Multi-step reaction with 8 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 0.5 h / 0 - 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

2.2: 1 h / 0 - 20 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 11 h / 20 °C

4.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / acetonitrile; water / 12 h / 20 °C

5.1: methanol; hexane / 0.5 h / 20 °C

6.1: cyclohexene; 20% palladium hydroxide on charcoal / methanol / 12 h / Inert atmosphere; Reflux

7.1: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

8.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 20% palladium hydroxide on charcoal; tetrabutyl ammonium fluoride; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; cyclohexene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/c2ob26712h

Reference yield:

: 1416133-39-5
3-benzyloxymethyl-1-(4-C-tert-butyldiphenylsilyloxymethyl-3,5-di-O-benzyl-β-D-ribofuranosyl)thymine

: 1416133-45-3
3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-5'-O-(4,4'-dimethoxytrityl)-4'-methoxycarbonyl-2'-O-methyl-5-methyluridine

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 0 °C / Inert atmosphere

1.2: 1 h / 0 - 20 °C

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 11 h / 20 °C

3.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / acetonitrile; water / 12 h / 20 °C

4.1: methanol; hexane / 0.5 h / 20 °C

5.1: cyclohexene; 20% palladium hydroxide on charcoal / methanol / 12 h / Inert atmosphere; Reflux

6.1: pyridine / 3 h / 0 - 20 °C / Inert atmosphere

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; 20% palladium hydroxide on charcoal; tetrabutyl ammonium fluoride; sodium hydride; N-ethyl-N,N-diisopropylamine; cyclohexene; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1039/c2ob26712h