3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione
• CAS No.: 153631-18-6
• Molecular Formula: C₃₅H₃₇N₃O₈
• Molecular Weight: 627.694
• Mol file: 153631-18-6.mol

Synonyms:3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione

Chemical Property of 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione

There total 6 articles about 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione 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:

2',3',5'-tri-O-benzoyluridine (3180-76-5) → 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione (153631-18-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / NaOMe / methanol / 24 h / Ambient temperature

2: 71 percent / pyridine / 1.25 h / Ambient temperature

3: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating

4: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h

With pyridine; tetra(n-butyl)ammonium hydroxide; sodium methylate; sodium hydride; In methanol; acetonitrile;

DOI:10.1002/jhet.5570300522

Reference yield:

thymin (65-71-4,28806-14-6,691841-57-3) → 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione (153631-18-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,1,1,3,3,3-hexamethyldisilazane, chlorotrimethyl silane / acetonitrile / 4 h / Heating

2: acetonitrile / 0.5 h / Heating

3: 90 percent / NaOMe / methanol / 24 h / Ambient temperature

4: 71 percent / pyridine / 1.25 h / Ambient temperature

5: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating

6: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h

With pyridine; chloro-trimethyl-silane; tetra(n-butyl)ammonium hydroxide; sodium methylate; sodium hydride; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; acetonitrile;

DOI:10.1002/jhet.5570300522

Reference yield:

1-((2R,3R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-3,4-dihydroxytetrahydrofuran-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (138239-62-0) → 3-(2-cyanoethyl)-1-<5-O--2-O-methyl-β-D-ribofuranosyl>-5-methyl-1H,3H-pyrimidine-2,4-dione (153631-18-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 65 percent / tetrabutylammonium hydroxide, pyridine / acetonitrile / 48 h / Heating

2: 1.) NaH / 1.) DMF, -40 deg C, 0.75 h, 2.) DMF, a) from -40 to -30 deg C, 0.75 h, b) RT, 4 h

With pyridine; tetra(n-butyl)ammonium hydroxide; sodium hydride; In acetonitrile;

DOI:10.1002/jhet.5570300522

upstream raw materials:

3-(2-cyanoethyl)-1-<5-O--β-D-ribofuranosyl>-5-methyl-1-1H,3H-pyrimidine-2,4-dione

methyl iodide

2',3',5'-tri-O-benzoyluridine

thymin

Downstream raw materials:

5'-O-(4,4'-dimethoxytrityl)-2'-O-methyl-5-methyluridine

2'-O-Methyl-5-methyluridine

(2R,3R,4R,5R)-2-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-((tert-butyldimethylsilyl)oxy)-5-(5-methyl-2,4-dioxo-3,4-dihyd ropyrimidin-1(2H)-yl)tetrahydrofuran-3-yl (2-cyanoethyl) diisopropylphosphoramidite