N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine
• CAS No.: 851085-35-3
• Molecular Formula: C₃₈H₃₄N₅O₈P
• Molecular Weight: 719.69

Synonyms:N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine

Chemical Property of N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine

There total 6 articles about N⁶-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine 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:

Benzoic acid (2R,3R,4R,5R)-5-(6-dibenzoylamino-purin-9-yl)-2-[(E)-2-(diphenoxy-phosphoryl)-vinyl]-4-hydroxy-4-methyl-tetrahydro-furan-3-yl ester → N6-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine (851085-35-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; under 1551.44 Torr;

DOI:10.1021/jm049029u

Reference yield:

5'-O-(tert-butyldimethylsilyl)-2'-C-methyladenosine → N6-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine (851085-35-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.05 g / pyridine / 16 h / 100 °C

2: 67 percent / tetrabutylammonium fluoride; AcOH / tetrahydrofuran / 16 h / 20 °C

3: 1,3-dicyclohexylcarbodiimide; pyridine / dimethylsulfoxide / 20 °C

4: dimethylsulfoxide

5: 132 mg / H₂ / Pd/C / methanol / 1551.44 Torr

With pyridine; tetrabutyl ammonium fluoride; hydrogen; acetic acid; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; dimethyl sulfoxide;

DOI:10.1021/jm049029u

Reference yield:

Benzoic acid (2S,3R,4R,5R)-5-(6-dibenzoylamino-purin-9-yl)-2-formyl-4-hydroxy-4-methyl-tetrahydro-furan-3-yl ester → N6-benzoyl-9-[3'-O-benzoyl-5',6'-dideoxy-6'-(diphenoxyphosphinyl)-2'-C-methyl-β-D-ribohexofuranosyl]adenine (851085-35-3)

Guidance literature:

Multi-step reaction with 2 steps

1: dimethylsulfoxide

2: 132 mg / H₂ / Pd/C / methanol / 1551.44 Torr

With hydrogen; palladium on activated charcoal; In methanol; dimethyl sulfoxide;

DOI:10.1021/jm049029u

upstream raw materials:

N⁶-dibenzoyl-9H-(3'-O-benzoyl-2'-C-methyl-β-D-ribofuranosyl)adenine

N⁶-dibenzoyl-9H-(3'-O-benzoyl-5'-O-tert-butyldimethylsilyl-2'-C-methyl-β-D-ribofuranosyl)adenine

2'-C-methyladenosine

Downstream raw materials:

{2-[(2R,3R,4R,5R)-5-(6-Benzoylamino-purin-9-yl)-3,4-dihydroxy-4-methyl-tetrahydro-furan-2-yl]-ethyl}-phosphonic acid dibenzyl ester

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