1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene

Base Information

• Chemical Name: 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene
• CAS No.: 1445870-38-1
• Molecular Formula: C₄₈H₅₃N₂O₈P
• Molecular Weight: 816.931
• Mol file: 1445870-38-1.mol

Synonyms:1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene

Chemical Property of 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene

There total 7 articles about 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene 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: 58.0%

1-benzoyloxy-2-[2-deoxy-5-O-(4,40-dimethoxytrityl)-β-D-ribofuranosyl]benzene (1445870-37-0) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene (1445870-38-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2013.05.107

Reference yield:

1-allyloxy-2-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene (1445870-25-6) → 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene (1445870-38-1)

Guidance literature:

Multi-step reaction with 5 steps

1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium tetrahydroborate / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

2: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

3: Pd(OH)2/C, 20%; cyclohexene / ethanol / 1.5 h / 70 °C

4: pyridine / 2 h / 20 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; sodium tetrahydroborate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Pd(OH)2/C, 20%; triethylamine; N-ethyl-N,N-diisopropylamine; cyclohexene; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/j.tet.2013.05.107

Reference yield:

2-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene (1445870-33-6) → 1-benzoyloxy-2-{3-O-[2-cyanoethoxy(diisopropylamino)phosphino]-2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranosyl}benzene (1445870-38-1)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere

2: Pd(OH)2/C, 20%; cyclohexene / ethanol / 1.5 h / 70 °C

3: pyridine / 2 h / 20 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

With pyridine; Pd(OH)2/C, 20%; triethylamine; N-ethyl-N,N-diisopropylamine; cyclohexene; In ethanol; dichloromethane;

DOI:10.1016/j.tet.2013.05.107

upstream raw materials:

1-allyloxy-2-(2-deoxy-3,5-di-O-benzyl-D-ribofuranosyl)benzene

2-(2-deoxy-3,5-di-O-benzyl-β-D-ribofuranosyl)-1-hydroxybenzene

3,5-di-O-benzyl-2-deoxy-D-ribofuranose

2-allyloxyphenyllithium