2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Base Information

• Chemical Name: 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose
• CAS No.: 1314971-25-9
• Molecular Formula: C₄₂H₅₁N₂O₇P
• Molecular Weight: 726.85
• Mol file: 1314971-25-9.mol

Synonyms:2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Chemical Property of 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

Chemical Property:

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

There total 8 articles about 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose 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: 97.0%

2-O-benzyl-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (1356682-32-0) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (1314971-25-9)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1016/j.bmcl.2017.10.070

Reference yield:

(4aR,7S,7aS)-2,2-ditert-butyl-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxasilin-7-ol (1314971-06-6) → 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (1314971-25-9)

Guidance literature:

Multi-step reaction with 4 steps

1: silica gel / ethyl acetate; hexane; acetonitrile

2: tetrabutyl ammonium fluoride; potassium fluoride / ethyl acetate; hexane; tetrahydrofuran

3: ethyl acetate; hexane; pyridine

4: N-ethyl-N,N-diisopropylamine; 1-methyl-1H-imidazole / ethyl acetate; hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

With 1-methyl-1H-imidazole; potassium fluoride; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; silica gel; In tetrahydrofuran; pyridine; hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate; acetonitrile;

Reference yield:

benzyl bromide (100-39-0) → 2-O-benzyl-3-O-[(2-cyanoethoxy)(N,N-diisopropylamino)phosphanyl]-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose (1314971-25-9)

Guidance literature:

Multi-step reaction with 4 steps

1: silica gel / ethyl acetate; hexane; acetonitrile

2: tetrabutyl ammonium fluoride; potassium fluoride / ethyl acetate; hexane; tetrahydrofuran

3: ethyl acetate; hexane; pyridine

4: N-ethyl-N,N-diisopropylamine; 1-methyl-1H-imidazole / ethyl acetate; hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran

With 1-methyl-1H-imidazole; potassium fluoride; tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; silica gel; In tetrahydrofuran; pyridine; hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate; acetonitrile;

upstream raw materials:

benzyl bromide

2-O-benzyl-1-deoxy-5-O-(4,4'-dimethoxytrityl)-D-ribofuranose

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

2-O-benzyl-1-deoxy-D-ribofuranose