1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine

Base Information

Chemical Name:1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine
CAS No.:1361928-18-8
Molecular Formula:C₄₇H₅₈F₃N₆O₁₀P
Molecular Weight:954.981
Hs Code.:

1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine

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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}-N4-Isobutyrylcytosine

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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}-N4-Isobutyrylcytosine

There total 15 articles about 1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine 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:

: 1361928-11-1
1-(2'-O-methyl-3',5'-di-O-benzyl-4'-C-trifluoroacetylaminomethyl-β-D-ribofuranosyl)uracil

: 1361928-18-8
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine

Guidance literature:: Multi-step reaction with 9 steps

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

2: pyridine / 24 h / 20 °C

3: pyridine / 20 °C

4: dmap; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice

5: ammonia / tetrahydrofuran; water / 0 - 20 °C

6: pyridine / 0.75 h / 0 - 20 °C

7: pyridine / 4 h / 0 °C

8: methanol / pyridine / 0.33 h

9: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.67 h / 20 °C

With methanol; dmap; palladium 10% on activated carbon; ammonia; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; ethanol; dichloromethane; water;
DOI:10.1021/jo202666m

Reference yield:

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

: 1361928-18-8
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine

Guidance literature:: Multi-step reaction with 8 steps

1: pyridine / 24 h / 20 °C

2: pyridine / 20 °C

3: dmap; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice

4: ammonia / tetrahydrofuran; water / 0 - 20 °C

5: pyridine / 0.75 h / 0 - 20 °C

6: pyridine / 4 h / 0 °C

7: methanol / pyridine / 0.33 h

8: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.67 h / 20 °C

With methanol; dmap; ammonia; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; dichloromethane; water;
DOI:10.1021/jo202666m

Reference yield:

: 250708-49-7
1,2-di-O-acetyl-5-azido-3-O-benzyl-4-C-[(benzyloxy)methyl]-5-deoxy-β-L-lyxofuranose

: 1361928-18-8
1-{2'-O-methyl-3'-O-[2-cyanoethoxy(diisopropylamino)phosphino]-4'-C-trifluoroacetylaminomethyl-5'-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}-N4-Isobutyrylcytosine

Guidance literature:: Multi-step reaction with 16 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / 80 °C

1.2: 0 - 80 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 6 h / 0 - 20 °C

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

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

4.2: 3 h / 20 °C / Inert atmosphere

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

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

7.1: triethylamine / tetrahydrofuran / 0 - 20 °C

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

9.1: pyridine / 24 h / 20 °C

10.1: pyridine / 20 °C

11.1: dmap; triethylamine / dichloromethane / 6 h / 20 °C / Cooling with ice

12.1: ammonia / tetrahydrofuran; water / 0 - 20 °C

13.1: pyridine / 0.75 h / 0 - 20 °C

14.1: pyridine / 4 h / 0 °C

15.1: methanol / pyridine / 0.33 h

16.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.67 h / 20 °C

With methanol; dmap; N,O-bis-(trimethylsilyl)-acetamide; ammonium cerium (IV) nitrate; palladium 10% on activated carbon; ammonia; water; hydrogen; sodium methylate; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1021/jo202666m