N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Base Information

• Chemical Name: N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine
• CAS No.: 847205-39-4
• Molecular Formula: C₄₈H₅₄N₁₀O₁₀Si
• Molecular Weight: 959.103

Synonyms:N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Chemical Property of N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

Chemical Property:

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Technology Process of N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

There total 2 articles about N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]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: 57.0%

N6-benzoyl-8-iodo-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine (292642-46-7) + N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine (244263-92-1) → N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine (847205-39-4)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; P(fur)3; In triethylamine; toluene; at 23 ℃; for 22h;

DOI:10.1002/hlca.200490269

Reference yield:

N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine (244263-89-6) → N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine (847205-39-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / TBAF / tetrahydrofuran; acetic acid / 0.75 h

2: 57 percent / [Pd₂(dba)3]; CuI; P(fur)3 / toluene; triethylamine / 22 h / 23 °C

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; copper(l) iodide; P(fur)3; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetic acid; triethylamine; toluene; 2: Sonogashira coupling;

DOI:10.1002/hlca.200490269

Reference yield: 77.0%

N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine (847205-39-4) → N6-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N6-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine (847205-40-7)

Guidance literature:

With 2,2,6,6-tetramethyl-piperidine; N-iodo-succinimide; n-butyllithium; N,N,N,N,N,N-hexamethylphosphoric triamide; In tetrahydrofuran; hexane; at -78 - 23 ℃;

DOI:10.1002/hlca.200490269

upstream raw materials:

N⁶-benzoyl-8-iodo-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosine

N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]adenine

N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-7-C-(trimethylsilyl)-β-D-allo-hept-6-ynofuranosyl]adenine

Downstream raw materials:

N⁶-benzoyl-2',3'-O-isopropylidene-5'-O-(triethylsilyl)adenosin-8-yl-(8->7'-C)-N⁶-benzoyl-9-[6,7-dideoxy-2,3-O-isopropylidene-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine

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