5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose

Base Information

• Chemical Name: 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose
• CAS No.: 130469-49-7
• Molecular Formula: C₂₄H₂₄O₉
• Molecular Weight: 456.449
• Mol file: 130469-49-7.mol

Synonyms:5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose

Chemical Property of 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose

There total 10 articles about 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-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:

acetic anhydride (108-24-7) + C20H20O7 → 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose (130469-49-7)

Guidance literature:

With pyridine; Yield given; Ambient temperature;

DOI:10.1021/jm00105a054

Reference yield:

5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose (69827-90-3) → 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose (130469-49-7)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. formic acid / 2 h / 55 °C

2: pyridine / 18 h / 20 °C

With pyridine; formic acid;

DOI:10.1081/NCN-200059338

Reference yield:

(3aR,5R,6aS)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-one (75783-45-8) → 5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-1,2-di-O-acetyl-β-D-ribofuranose (130469-49-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane / 0.5 h / 50 °C

1.2: 1.33 h / 50 °C

2.1: borane-THF / tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

2.2: 2 h / 0 - 20 °C / Inert atmosphere

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.25 h / 20 °C

4.1: pyridine / 1.67 h / 0 - 20 °C

5.1: trifluoroacetic acid / water / 1.5 h / 20 °C

6.1: dmap; pyridine / 2 h / 20 °C / Inert atmosphere

With pyridine; dmap; borane-THF; tetrabutyl ammonium fluoride; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; n-heptane; water;

upstream raw materials:

acetic anhydride

5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose

benzoyl chloride

(3aR,5R,6aS)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]-2,2-dimethyltetrahydro-2H-furo[2,3-d][1,3]dioxol-6-one

Downstream raw materials:

5'-O-benzoyl-3'-deoxy-3'-[(benzoyloxy)methyl]-2'-O-acetyl-5-methyluridine

6-chloro-9-<5-O-benzoyl-3-deoxy-3-<(benzoyloxy)methyl>-2-O-acetyl-β-D-ribofuranosyl>-9H-purine

Thiocarbonic acid O-[(2R,3R,4R,5S)-2-(6-amino-purin-9-yl)-4,5-bis-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-3-yl] ester O-phenyl ester

6-amino-9-<3-deoxy-3-(hydroxymethyl)-β-D-ribofuranosyl>-9H-purine