5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl

Base Information

• Chemical Name: 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl
• CAS No.: 166411-46-7
• Molecular Formula: C₁₂H₁₂BrFO₃
• Molecular Weight: 303.128
• Mol file: 166411-46-7.mol

Synonyms:5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl

Chemical Property of 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl

There total 6 articles about 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl 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:

5-O-benzoyl-2,3-dideoxy-1,2-difluoro-α-L-threo-pentofuranosyl (166411-45-6) → 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl (166411-46-7)

Guidance literature:

With hydrogen bromide; acetic acid; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1080/07328319908044878

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose (166411-40-1) → 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl (166411-46-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / ethanol / 2 h / Heating

2: 94 percent / NaCNBH₃; methyl orange; HCl / methanol; tetrahydrofuran / 2 h / 20 °C / pH 3

3: 69 percent / NaOAc*3H₂O / ethanol / 1 h / Heating

4: 68 percent / 80 percent AcOH / 4 h / 100 °C

5: 46 percent / DAST / CH₂Cl₂ / 10 h / 20 °C

6: 45 percent HBr; HOAc / CH₂Cl₂ / 1 h / 20 °C

With hydrogenchloride; hydrogen bromide; sodium acetate; methyl orange; sodium cyanoborohydride; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Condensation / 2: Reduction / 3: Elimination / 4: Ring cleavage / 5: Fluorination / 6: Bromination;

DOI:10.1080/07328319908044878

Reference yield:

5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-L-erythro-pentofuranose (166411-43-4) → 5-O-benzoyl-1-bromo-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl (166411-46-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / 80 percent AcOH / 4 h / 100 °C

2: 46 percent / DAST / CH₂Cl₂ / 10 h / 20 °C

3: 45 percent HBr; HOAc / CH₂Cl₂ / 1 h / 20 °C

With hydrogen bromide; acetic acid; 4,4'-diaminostilbene-2,2'-disulfonic acid; In dichloromethane; 1: Ring cleavage / 2: Fluorination / 3: Bromination;

DOI:10.1080/07328319908044878

upstream raw materials:

5-O-benzoyl-2,3-dideoxy-1,2-difluoro-α-L-threo-pentofuranosyl

5-O-benzoyl-1,2-O-isopropylidene-α-L-erythro-pentofuranose-3-ulose

5-O-benzoyl-3-deoxy-1,2-O-isopropylidene-α-L-erythro-pentofuranose

5-O-benzoyl-1,2-O-isopropylidene-p-toluenesulfonylhydrazone-α-L-erythro-pentofurano-3-ulose

Downstream raw materials:

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-α-L-threo-pentofuranosyl)uracil

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)uracil

1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)cytosine

5-methyl-1-(5-O-benzoyl-2,3-dideoxy-2-fluoro-β-L-threo-pentofuranosyl)cytosine

Refernces