9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine

Base Information

• Chemical Name: 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine
• CAS No.: 161496-51-1
• Molecular Formula: C₂₆H₂₁N₅O₆
• Molecular Weight: 499.483
• Mol file: 161496-51-1.mol

Synonyms:9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine

Chemical Property of 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine

There total 1 articles about 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine 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 acid (2R,3S,5R)-5-(6-dibenzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester (89000-77-1) → 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine (161496-51-1)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 ℃; for 0.5h;

DOI:10.1055/s-1994-25686

Reference yield:

Phenylselenyl chloride (5707-04-0) + 9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine (161496-51-1) → 9-(3-O-acetyl-2-deoxy-4-phenylseleno-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine + 9-(3-O-acetyl-2-deoxy-4-phenylseleno-α-L-threo-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine

Guidance literature:

With triethylamine; In dichloromethane; Yield given. Yields of byproduct given. Title compound not separated from byproducts; -78 deg C, 30 min; -78 deg C to r.t.; r.t., 2 h;

DOI:10.1055/s-1994-25686

Reference yield:

9-(3-O-acetyl-2-deoxy-β-D-erythro-pento-5-aldo-1,4-furanosyl)-6,6-N,N-dibenzoyladenine (161496-51-1) → 6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4'-phenylseleno-adenosine (161496-55-5)

Guidance literature:

Multi-step reaction with 3 steps

1: NEt₃ / CH₂Cl₂ / -78 deg C to 0 deg C

2: Bu₄NBH₃(CN) / tetrahydrofuran / -78 deg C to 0 deg C

3: 2.) NaOMe; NH₃ / 1.) pyridine, 20 deg C; 2.) MeOH, 10 min; MeOH, 0 deg C, 50 min

With ammonia; sodium methylate; tetrabutylammonium (cyano)trihydroborate; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

Acetic acid (2R,3S,5R)-5-(6-dibenzoylamino-purin-9-yl)-2-hydroxymethyl-tetrahydro-furan-3-yl ester

Downstream raw materials:

6-N-benzoyl-2'-deoxy-5'-O-(4,4'-dimethoxytriphenylmethyl)-4'-phenylseleno-adenosine

3'-O-acetyl-2'-deoxy-6,6-N,N-dibenzoyl-4'-phenylseleno-adenosine