1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine

Base Information

• Chemical Name: 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine
• CAS No.: 159228-08-7
• Molecular Formula: C₂₇H₂₂N₄O₉
• Molecular Weight: 546.493
• Mol file: 159228-08-7.mol

Synonyms:

Chemical Property of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine

There total 1 articles about 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine 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:

Lumazine (487-21-8) + (3R,4S,5R)-4-(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate (85026-60-4) → 1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine (159228-08-7)

Guidance literature:

With ammonium sulfate; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane; Yield given. Multistep reaction; 1.) reflux, 6 h, 2.) EtOAc, RT, 2 h;

DOI:10.1080/15257779408013278

Reference yield: 86.0%

1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine (159228-08-7) → 1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine (159228-09-8)

Guidance literature:

With pyridine; hydrazine hydrate; acetic acid; Ambient temperature;

DOI:10.1080/15257779408013278

Reference yield:

1-(2-O-acetyl-3,5-di-O-benzoyl-β-D-threo-pentofuranosyl)-lumazine (159228-08-7) → 1-(2-bromo-2-deoxy-3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / pyridine, acetic acid, hydrazine hydrate / Ambient temperature

2: 84 percent / pyridine / 2 h / 0 °C

3: 93 percent / DBU / CH₂Cl₂ / 0.25 h / Heating

4: 67 percent / lithium bromide, HBr / dimethylformamide; acetic acid / 1 h / Ambient temperature

With pyridine; hydrogen bromide; hydrazine hydrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium bromide; In pyridine; dichloromethane; acetic acid; N,N-dimethyl-formamide;

DOI:10.1080/15257779408013278

upstream raw materials:

Lumazine

(3R,4S,5R)-4-(benzoyloxy)-5-((benzoyloxy)methyl)tetrahydrofuran-2,3-diyl diacetate

Downstream raw materials:

1-(3,5-di-O-benzoyl-β-D-xylofuranosyl)-lumazine

2,2'-anhydro-1-(3,5-di-O-benzoyl-β-D-lyxofuranosyl)-lumazine

1-(3,5-di-O-benzoyl-2-O-mesyl-β-D-xylofuranosyl)-lumazine

1-(3,5-di-O-benzoyl-2-O-phenoxythiocarbonyl-β-D-xylofuranosyl)-lumazine

Refernces