1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil

Base Information

• Chemical Name: 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil
• CAS No.: 338742-53-3
• Molecular Formula: C₂₃H₂₄N₂O₄S
• Molecular Weight: 424.521
• Mol file: 338742-53-3.mol

Synonyms:1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil

Chemical Property of 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil

There total 3 articles about 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil 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: 59.0%

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside (136737-52-5) + O,O'-bis-(trimethylsilyl)uracil (10457-14-4) → 1-(3,5-di-O-benzyl-2-deoxy-4-thio-α-L-threo-pentofuranosyl)uracil + 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil (338742-53-3)

Guidance literature:

With N-iodo-succinimide; 4 A molecular sieve; In acetonitrile; at 20 ℃; for 2h;

DOI:10.1002/1099-0690(200103)2001:6<1077::AID-EJOC1077>3.0.CO;2-0

Reference yield:

3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal (134700-11-1) → 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil (338742-53-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 22.0 g / pyridine / 24 h / 20 °C

2: 85 percent / nBu₄NI; BaCO₃ / dioxane / 2.5 h / Heating

3: 59 percent / NIS; mol. sieves 4 Angstroem / acetonitrile / 2 h / 20 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; barium carbonate; In 1,4-dioxane; acetonitrile;

DOI:10.1002/1099-0690(200103)2001:6<1077::AID-EJOC1077>3.0.CO;2-0

Reference yield:

3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal (136737-51-4) → 1-(3,5-di-O-benzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)uracil (338742-53-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / nBu₄NI; BaCO₃ / dioxane / 2.5 h / Heating

2: 59 percent / NIS; mol. sieves 4 Angstroem / acetonitrile / 2 h / 20 °C

With N-iodo-succinimide; 4 A molecular sieve; tetra-(n-butyl)ammonium iodide; barium carbonate; In 1,4-dioxane; acetonitrile;

DOI:10.1002/1099-0690(200103)2001:6<1077::AID-EJOC1077>3.0.CO;2-0

upstream raw materials:

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside

O,O'-bis-(trimethylsilyl)uracil

3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal

3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal