1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil

Base Information

• Chemical Name: 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil
• CAS No.: 151503-22-9
• Molecular Formula: C₂₅H₂₄N₂O₆S
• Molecular Weight: 480.541
• Mol file: 151503-22-9.mol

Synonyms:1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil

Chemical Property of 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil

There total 3 articles about 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil 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: 94.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine (32865-74-0) → 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil (151503-22-9)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at -40 ℃;

DOI:10.1016/S0040-4039(00)79235-5

Reference yield: 68.0%

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) + 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine (32865-74-0) → 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil (151503-22-9) + 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-ribofuranosyl)-2-thiouracil (152310-75-3)

Guidance literature:

With tin(IV) chloride; In 1,2-dichloro-ethane; at 35 ℃; for 2h;

DOI:10.1080/07328319308021507

Reference yield:

C28H32N2O6SSi + 4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine (32865-74-0) → 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-2-thiouracil (151503-22-9) + 3-(2'-deoxy-3',5'-di-O-(p-toluoyl)-β-D-erythro-ribofuranosyl)-uracil + 1-(2'-deoxy-3',5'-di-O-(p-toluoyl)-α-D-erythro-ribofuranosyl)-2-thiouracil (152310-75-3)

Guidance literature:

With tin(IV) chloride; at -30 ℃; Yield given. Yields of byproduct given;

DOI:10.1080/07328319308021507

upstream raw materials:

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

4-trimethylsilyloxy-2-trimethylsilylthiopyrimidine

Downstream raw materials:

1-(2'-deoxy-5'-O-4,4'-dimethoxytrityl-β-D-erythro-ribofuranosyl)-2-thiouracil

1-(2'-deoxy-3'-O-(2-chlorophenyl2-cyanoethyl)-phosphate-β-D-erythro-ribofuranosyl)-2-thiouracil

1-{(2R,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-tetrahydro-furan-2-yl}-1H-pyrimidin-4-one