N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine

Base Information

• Chemical Name: N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine
• CAS No.: 424822-64-0
• Molecular Formula: C₃₄H₅₁N₅O₆Si₃
• Molecular Weight: 710.065

Synonyms:N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine

Chemical Property of N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine

There total 1 articles about N⁶-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}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: 95.0%

N-[9-((2R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-oxo-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-6-yl]-benzamide (100034-54-6) + trimethylsilylacetylene (1066-54-2) → N6-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine (424822-64-0)

Guidance literature:

trimethylsilylacetylene; With n-butyllithium; In tetrahydrofuran; hexane; at -17 ℃; for 0.5h;

N-[9-((2R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-oxo-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-6-yl]-benzamide; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

DOI:10.1002/1522-2675(200201)85:1<224::AID-HLCA224>3.0.CO;2-L

Reference yield:

monomethyl oxalyl chloride (5781-53-3) + N6-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine (424822-64-0) → Oxalic acid (2R,3S,3aR,9aR)-2-(6-benzoylamino-purin-9-yl)-5,5,7,7-tetraisopropyl-3-trimethylsilanylethynyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester methyl ester

Guidance literature:

With dmap; In dichloromethane; at -17 - 20 ℃; for 12h;

DOI:10.1002/1522-2675(200201)85:1<224::AID-HLCA224>3.0.CO;2-L

Reference yield:

N6-benzoyl-9-{3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine (424822-64-0) → 9-(2'-deoxy-2'-C-ethynyl-β-D-arabinofuranosyl)-N6-(phenoxyacetyl)adenine (205500-35-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: DMAP / CH₂Cl₂ / 12 h / -17 - 20 °C

2.1: 0.68 g / Bu₃SnH; AIBN / toluene / 3 h / 95 °C

3.1: triethyloxonium tetrafluoroborate / CH₂Cl₂ / 3 h / 20 °C

3.2: 74 percent / CH₂Cl₂ / 19 h / 20 °C

4.1: 95 percent / Bu₄NF / tetrahydrofuran; acetic acid / 1 h / 20 °C

With dmap; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; triethyloxonium fluoroborate; In tetrahydrofuran; dichloromethane; acetic acid; toluene;

DOI:10.1002/1522-2675(200201)85:1<224::AID-HLCA224>3.0.CO;2-L

upstream raw materials:

N-[9-((2R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-oxo-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-6-yl]-benzamide

trimethylsilylacetylene

Downstream raw materials:

9-(2'-deoxy-2'-C-ethynyl-β-D-arabinofuranosyl)-N⁶-(phenoxyacetyl)adenine

9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N⁶-(phenoxyacetyl)adenine

9-[2'-deoxy-5'-O-(4,4'-dimethoxytrityl)-2'-C-ethynyl-β-D-arabinofuranosyl]-N⁶-(phenoxyacetyl)adenine

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