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

Base Information

• Chemical Name: 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N⁶-(phenoxyacetyl)adenine
• CAS No.: 205500-34-1
• Molecular Formula: C₃₅H₅₃N₅O₆Si₃
• Molecular Weight: 724.092

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N⁶-(phenoxyacetyl)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: 74.0%

1-(phenoxyacetyl)-1H-imidazole (110009-60-4) + 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine (205500-33-0) → 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N6-(phenoxyacetyl)adenine (205500-34-1)

Guidance literature:

1-(phenoxyacetyl)-1H-imidazole; With triethyloxonium fluoroborate; In dichloromethane; at 20 ℃; for 3h;

9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}adenine; In dichloromethane; at 20 ℃; for 19h;

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

Reference yield:

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) → 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N6-(phenoxyacetyl)adenine (205500-34-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -17 °C

1.2: 95 percent / hexane; tetrahydrofuran / 3 h / -78 °C

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

3.1: 0.68 g / Bu₃SnH; AIBN / toluene / 3 h / 95 °C

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

4.2: 74 percent / CH₂Cl₂ / 19 h / 20 °C

With dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethyloxonium fluoroborate; In tetrahydrofuran; hexane; dichloromethane; toluene;

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

Reference yield:

3',5'-O-(tetraisopropyldisiloxane-1,3-diyl)-N6-benzoyladenosine (79154-57-7) → 9-{2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2'-C-[(trimethylsilyl)ethynyl]-β-D-arabinofuranosyl}-N6-(phenoxyacetyl)adenine (205500-34-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 20 h / Ambient temperature

2: 95 percent / BuLi / tetrahydrofuran / 3 h / -78 °C

3: 1.) CH₃O₂CCOCl, DMAP, 2.) Bu₃SnH, AIBN / 1.) CH₂Cl₂, RT, 12 h, 2.) toluene, 90 deg C, 4 h

4: 1.) Et₃O⁺BF₄^- / 1.) CH₂Cl₂, RT, 3h, 2.) CH₂Cl₂, RT, 19h

With monomethyl oxalyl chloride; dmap; n-butyllithium; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; triethyloxonium fluoroborate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0960-894X(98)00060-2

upstream raw materials:

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

1-(phenoxyacetyl)-1H-imidazole

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

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