arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

Base Information

• Chemical Name: arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate
• CAS No.: 211441-78-0
• Molecular Formula: C₃₄H₃₆N₅O₁₁P
• Molecular Weight: 721.661
• Mol file: 211441-78-0.mol

Synonyms:arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

Chemical Property of arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

There total 7 articles about arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate 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: 80.0%

3',5'-O-1,1,3,3-tetraisopropyl-1,3-disiloxyl-arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate (211441-74-6) → arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate (211441-78-0)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(98)00457-8

Reference yield:

phenazine methosulfate (299-11-6) → arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate (211441-78-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 32 percent / methanol / 72 h / 25 °C

2.1: pyridine / 0.5 h / 25 °C

3.1: pyridine / 1 h / 25 °C

4.1: aq. NH₃ / pyridine / 0.5 h / 25 °C

5.1: tetrazole / acetonitrile / 1 h / 20 °C

5.2: 70 percent / I₂ / tetrahydrofuran; pyridine; H₂O / 0.5 h / 20 °C

6.1: 80 percent / (n-Bu)4NF*H₂O / tetrahydrofuran / 0.5 h / 0 °C

With 1H-tetrazole; ammonium hydroxide; tetrabutyl ammonium fluoride; In tetrahydrofuran; pyridine; methanol; acetonitrile; 1.1: Addition / 2.1: Addition / 3.1: Addition / 4.1: Hydrolysis / 5.1: Addition / 5.2: Oxidation / 6.1: Hydrolysis;

DOI:10.1016/S0040-4020(98)00457-8

Reference yield:

Diisopropyl-phosphoramidous acid (2R,3S,3aR,9aR)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester methyl ester (183273-98-5) → arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate (211441-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: tetrazole / acetonitrile / 1 h / 20 °C

1.2: 70 percent / I₂ / tetrahydrofuran; pyridine; H₂O / 0.5 h / 20 °C

2.1: 80 percent / (n-Bu)4NF*H₂O / tetrahydrofuran / 0.5 h / 0 °C

With 1H-tetrazole; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetonitrile; 1.1: Addition / 1.2: Oxidation / 2.1: Hydrolysis;

DOI:10.1016/S0040-4020(98)00457-8

upstream raw materials:

3',5'-O-1,1,3,3-tetraisopropyl-1,3-disiloxyl-arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

phenazine methosulfate

Diisopropyl-phosphoramidous acid (2R,3S,3aR,9aR)-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester methyl ester

4-(phenazin-2-ylamino)-butan-1-ol

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-arabinouridine 2'-(O-methyl)-(O-2-(N-methyl)amino phenazine-4-N-butyl) phosphate

Refernces