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

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]-8-iodoadenine
• CAS No.: 847205-40-7
• Molecular Formula: C₄₈H₅₃IN₁₀O₁₀Si
• Molecular Weight: 1085

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]-8-iodoadenine

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]-8-iodoadenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

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]-8-iodoadenine

There total 3 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]-8-iodoadenine 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: 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

Reference yield: 10.0%

lithium diisopropyl amide (4111-54-0) + 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) + N6-benzoyl-2-(diisopropylamino)-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

Guidance literature:

With N-iodo-succinimide;

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]-8-iodoadenine (847205-40-7)

Guidance literature:

Multi-step reaction with 3 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

3: 36 percent / NIS

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

DOI:10.1002/hlca.200490269

upstream raw materials:

lithium diisopropyl amide

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

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-5-O-(triethylsilyl)-β-D-allo-hept-6-ynofuranosyl]-8-iodoadenine

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