1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose

Base Information

• Chemical Name: 1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose
• CAS No.: 872051-20-2
• Molecular Formula: C₂₇H₂₅BrO₅
• Molecular Weight: 509.397
• Mol file: 872051-20-2.mol

Synonyms:1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose

Chemical Property of 1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose

There total 1 articles about 1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose 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: 12.0%

1,3-dibromobenzene (108-36-1) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 1β-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose (872051-19-9) + 1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose (872051-20-2)

Guidance literature:

1,3-dibromobenzene; With magnesium; ethylene dibromide; In tetrahydrofuran; at 65 ℃; for 1h;

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200500607

Reference yield: 32.0%

1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose (872051-20-2) → 1β-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose (872051-19-9)

Guidance literature:

With sulfuric acid; trifluoroacetic acid; benzenesulfonic acid; In dichloromethane; at 40 ℃; for 24h;

DOI:10.1002/ejoc.200500607

Reference yield:

1α-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose (872051-20-2) → 1,2-dideoxy-1β-[3-(4-fluorophenyl)phenyl]-D-ribofuranose

Guidance literature:

Multi-step reaction with 3 steps

1: 32 percent / benzenesulfonic acid; trifluoroacetic acid; H₂SO₄ / CH₂Cl₂ / 24 h / 40 °C

2: 68 percent / K₂CO₃; Pd(PPh₃)4 / toluene / 12 h / 100 °C

3: 83 percent / NaOMe / methanol / 20 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sulfuric acid; sodium methylate; potassium carbonate; trifluoroacetic acid; benzenesulfonic acid; In methanol; dichloromethane; toluene; 2: Suzuki-Miyaura cross-coupling reaction;

DOI:10.1002/ejoc.200500607

upstream raw materials:

1,3-dibromobenzene

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

Downstream raw materials:

1β-(3-bromophenyl)-1,2-dideoxy-3,5-di-O-(4-toluoyl)-D-ribofuranose

1,2-dideoxy-1β-[3-(4-fluorophenyl)phenyl]-3,5-di-O-(4-toluoyl)-D-ribofuranose

1,2-dideoxy-1β-[3-(2-naphthyl)phenyl]-3,5-di-O-(4-toluoyl)-D-ribofuranose