1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione
• CAS No.: 219613-62-4
• Molecular Formula: C₂₃H₂₄N₂O₄S
• Molecular Weight: 424.521
• Mol file: 219613-62-4.mol

Synonyms:1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property of 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

There total 2 articles about 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-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: 82.0%

1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose (134700-26-8) → 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (219613-62-4)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In 1,2-dichloro-ethane; Ambient temperature;

DOI:10.1016/S0040-4039(00)78345-6

Reference yield:

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside (134938-97-9) → 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (219613-62-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / acetic acid

2: 82 percent / CF₃SO₃SiMe₃ / 1,2-dichloro-ethane / Ambient temperature

With trimethylsilyl trifluoromethanesulfonate; In acetic acid; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)78345-6

Reference yield: 50.0%

benzoyl chloride (98-88-4) + 1-((4S,5R)-4-Benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (219613-62-4) → 3-Benzoyl-1-((2R,4S,5R)-4-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (166812-97-1) + 3-Benzoyl-1-((2S,4S,5R)-4-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione (166813-00-9)

Guidance literature:

With pyridine;

DOI:10.1016/S0040-4039(00)78345-6

upstream raw materials:

1-O-acetyl-2-deoxy-3,5-di-O-benzyl-4-thio-D-erythro-pentafuranose

benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside

Downstream raw materials:

3-Benzoyl-1-((2R,4S,5R)-4-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

3-Benzoyl-1-((2S,4S,5R)-4-benzyloxy-5-benzyloxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidine-2,4-dione

1-(2-Deoxy-4-thio-β-D-ribofuranosyl)uracil

3',5'-di-O-benzyl-4'-thio-2'-deoxyuridine