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

Base Information

• Chemical Name: 9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine
• CAS No.: 130250-09-8
• Molecular Formula: C₃₂H₂₇ClN₄O₆
• Molecular Weight: 599.043
• Mol file: 130250-09-8.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about 9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine 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: 78.0%

1,2,5-tri-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-α,β-D-ribofuranose (130250-05-4,130250-11-2) + 6-chloropurine (87-42-3) → 9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine (130250-09-8)

Guidance literature:

With benzenesulfonamide; TMSTf; In acetonitrile; for 1h;

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

Reference yield:

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose (6698-46-0) → 9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine (130250-09-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, -40 deg C

2: 91 percent / 5percent Pd/C, H₂ / ethanol / 4 h / 2585.7 Torr

3: 70 percent / 1N HCl / dioxane / 3 h

4: 95 percent / pyridine / 1.5 h / Ambient temperature

5: 78 percent / BSA, TMSTf / acetonitrile / 1 h

With pyridine; hydrogenchloride; benzenesulfonamide; palladium on activated charcoal; n-butyllithium; TMSTf; hydrogen; In 1,4-dioxane; ethanol; acetonitrile;

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

Reference yield:

5-O-benzoyl-3-deoxy-3-<(benzyloxy)methyl>-α,β-D-ribofuranose (130250-08-7,130250-10-1) → 9-<3'-deoxy-3'-<(benzyloxy)methyl>-2,5-di-O-benzoyl-β-D-ribofuranosyl>-6-chloropurine (130250-09-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 95 percent / pyridine / 1.5 h / Ambient temperature

2: 78 percent / BSA, TMSTf / acetonitrile / 1 h

With pyridine; benzenesulfonamide; TMSTf; In acetonitrile;

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

upstream raw materials:

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

6-chloropurine

5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranos-3-ulose

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

Downstream raw materials:

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