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

Base Information

• Chemical Name: 5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose
• CAS No.: 69827-90-3
• Molecular Formula: C₂₃H₂₄O₇
• Molecular Weight: 412.439
• Mol file: 69827-90-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 14 articles about 5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose 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: 95.0%

((3aR,5S,6R,6aR)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methanol (69827-89-0) + benzoyl chloride (98-88-4) → 5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose (69827-90-3)

Guidance literature:

With pyridine; at 0 ℃;

DOI:10.1081/NCN-120022679

Reference yield:

3-deoxy-3-<(benzoyloxy)methyl>-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (130469-40-8) → 5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose (69827-90-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.47 g / 0.06 N aq. HCl / methanol / 1 h / 55 °C

2: 1.) NaIO₄, NaHCO₃, 2.) sodium borohydride / 1.) ethanol, water, RT, 3 h, 2.) RT, 1 h

3: pyridine / 1 h / 0 °C

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium periodate; sodium hydrogencarbonate; In methanol;

DOI:10.1021/jm00105a054

Reference yield:

3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose (130469-48-6) + benzoyl chloride (98-88-4) → 5-O-benzoyl-3-C-benzoyloxymethyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-pentofuranose (69827-90-3)

Guidance literature:

With pyridine; at 0 ℃; for 1h;

DOI:10.1021/jm00105a054

upstream raw materials:

3-deoxy-3-<(benzoyloxy)methyl>-1,2-isopropylidene-α-ribofuranose

benzoyl chloride

((3aR,5S,6R,6aR)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-methanol

3-deoxy-3-(hydroxymethyl)-5-O-<(tert-butyldimethyl)silyl>-1,2-O-isopropylidene-α-D-ribofuranose

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

C₂₇H₂₃FO₇