(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane
• CAS No.: 1092803-51-4
• Molecular Formula: C₄₉H₅₄N₅O₈P
• Molecular Weight: 871.97
• Mol file: 1092803-51-4.mol

Synonyms:(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane

There total 6 articles about (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane 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: 88.0%

(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-2-oxabicyclo[2.2.1]heptane (1092803-50-3) + N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite (102691-36-1) → (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane (1092803-51-4)

Guidance literature:

With 1-methyl-1H-imidazole; 2H-tetrazole; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1021/ja105875e

Reference yield:

(1R,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane (1092803-46-7) → (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane (1092803-51-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridine / 16 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h / 20 °C

3.1: triethylamine; trichlorophosphate; 1,2,4-Triazole / acetonitrile / 5 h / 20 °C

3.2: 4 h / 20 °C

4.1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 16 h / 20 °C

5.1: N,N-dimethyl-formamide / 24 h / 20 °C

6.1: 1H-tetrazole; 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; 1-methyl-1H-imidazole; 1H-tetrazole; triethylamine tris(hydrogen fluoride); triethylamine; trichlorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide; acetonitrile;

Reference yield:

C39H47N3O6Si (1092804-55-1) → (1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-7-[cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-5-methylene-2-oxabicyclo[2.2.1]heptane (1092803-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: triethylamine; triethylamine tris(hydrogen fluoride) / tetrahydrofuran / 16 h / 20 °C

2: N,N-dimethyl-formamide / 24 h / 20 °C

3: 1H-tetrazole; 1-methyl-1H-imidazole / N,N-dimethyl-formamide / 6 h / 20 °C

With 1-methyl-1H-imidazole; 1H-tetrazole; triethylamine tris(hydrogen fluoride); triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide;

upstream raw materials:

(1R,3R,4R,7S)-3-(4-N-benzoylcytosin-1-yl)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-2-oxabicyclo[2.2.1]heptane

N,N,N',N'-tetraisopropyl 2-cyanoethylphosphorodiamidite

(1R,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-5-methylene-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane