1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine

Base Information

• Chemical Name: 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine
• CAS No.: 649571-02-8
• Molecular Formula: C₂₉H₄₆N₂O₅SSeSi₂
• Molecular Weight: 669.892
• Mol file: 649571-02-8.mol

Synonyms:1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine

Chemical Property of 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine

There total 5 articles about 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine 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: 87.0%

Phenylselenyl chloride (5707-04-0) + 2,4-bis(trimethylsiloxy)-5-methylpyrimidine (7288-28-0) + 1,4-anhydro-2-deoxy-2-methyl-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol (649571-01-7) → 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine (649571-02-8)

Guidance literature:

In dichloromethane; acetonitrile; at 0 ℃; for 4h;

DOI:10.1021/ol040035u

Reference yield:

1,4-anhydro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisiloxan-1,3-diyl)-4-thio-D-erythro-pent-1-enitol (209048-61-3) → 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine (649571-02-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: LDA / tetrahydrofuran / 0.5 h / -70 °C

1.2: 86 percent / PhSO₂Cl / tetrahydrofuran / 0.5 h / -70 °C

2.1: LTMP / tetrahydrofuran / 0.5 h / -70 °C

2.2: 71 percent / tetrahydrofuran / 0.5 h / -70 °C

3.1: 81 percent / liquid NH₃; Na / diethyl ether / 0.5 h / -80 °C

4.1: 87 percent / acetonitrile; CH₂Cl₂ / 4 h / 0 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ol040035u

Reference yield:

1,4-anhydro-1-chloro-2-deoxy-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol (649570-99-0) → 1-[2-deoxy-2-methyl-2-phenylseleno-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]thymine (649571-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LTMP / tetrahydrofuran / 0.5 h / -70 °C

1.2: 71 percent / tetrahydrofuran / 0.5 h / -70 °C

2.1: 81 percent / liquid NH₃; Na / diethyl ether / 0.5 h / -80 °C

3.1: 87 percent / acetonitrile; CH₂Cl₂ / 4 h / 0 °C

With 2,2,6,6-tetramethylpiperidinyl-lithium; ammonia; sodium; In tetrahydrofuran; diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/ol040035u

upstream raw materials:

Phenylselenyl chloride

2,4-bis(trimethylsiloxy)-5-methylpyrimidine

1,4-anhydro-2-deoxy-2-methyl-3,5-O-(1,1,3,3-tetraisopropyldisioxane-1,3-diyl)-4-thio-D-erythro-pento-1-enitol

thymin