5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

Base Information

• Chemical Name: 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose
• CAS No.: 130250-07-6
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 130250-07-6.mol

Synonyms:5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property of 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose

There total 11 articles about 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-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: 93.0%

benzoyl chloride (98-88-4) + 3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose (604801-31-2) → 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose (130250-07-6)

Guidance literature:

With pyridine; at 20 ℃; for 2h;

DOI:10.1080/15257770801944436

Reference yield: 91.0%

5-O-benzoyl-1,2-O-isopropylidene-3-C-<(benzyloxy)methylene>-α-D-ribofuranose (130250-06-5) → 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose (130250-07-6)

Guidance literature:

With palladium on activated charcoal; hydrogen; In ethanol; for 4h; under 2585.7 Torr;

DOI:10.1016/S0040-4039(00)94705-1

Reference yield:

benzyl bromide (100-39-0) → 5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-1,2-O-isopropylidene-α-D-ribofuranose (130250-07-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) NaH / 1.) DMF, RT, 40 min, 2.) DMF, RT, 13 h

2: 0.8 N H₂SO₄ / methanol / 48 h / Ambient temperature

3: NaIO₄ / methanol / 2.5 h / Ambient temperature

4: NaBH₄ / methanol / 2 h / Ambient temperature

5: pyridine / 2 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium periodate; sulfuric acid; sodium hydride; In methanol;

DOI:10.1016/0040-4020(96)00007-5

upstream raw materials:

5-O-benzoyl-1,2-O-isopropylidene-3-C-<(benzyloxy)methylene>-α-D-ribofuranose

benzoyl chloride

3-C-(benzyloxymethyl)-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

benzyl bromide

Downstream raw materials:

5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-α,β-D-ribofuranose

(3R,4S,5R)-5-<(benzoyloxy)methyl>-4-<(benzyloxy)methyl>tetrahydrofuran-3-ol

methyl 5-O-benzoyl-3-C-(benzyloxymethyl)-3-deoxy-β-D-ribofuranoside

9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine