Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester
• CAS No.: 169886-65-1
• Molecular Formula: C₃₂H₄₇N₅O₉Si₂
• Molecular Weight: 701.924
• Mol file: 169886-65-1.mol

Synonyms:Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester

Chemical Property of Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester

There total 3 articles about Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester 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: 79.0%

acetic anhydride (108-24-7) + N-[9-((2R,3S,3aS,9aR)-3-Hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide (169886-61-7) → Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester (169886-65-1)

Guidance literature:

With dmap; In pyridine; dichloromethane; for 2h; Ambient temperature;

DOI:10.1080/15257779508010720

Reference yield:

N-[6-Oxo-9-((2R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-oxo-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide → Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester (169886-65-1)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / tetrahydrofuran; aq. ethanol / 1 h / -5 °C

2: 79 percent / DMAP / CH₂Cl₂; pyridine / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; In tetrahydrofuran; pyridine; ethanol; dichloromethane;

DOI:10.1080/15257779508010720

Reference yield:

N2-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine (131474-72-1) → Acetic acid (2R,3S,3aR,9aR)-5,5,7,7-tetraisopropyl-2-[6-oxo-2-(2-phenoxy-acetylamino)-1,6-dihydro-purin-9-yl]-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yl ester (169886-65-1)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin 12-I-5 periodinane oxidant / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) room temperature, 2 h

2: NaBH₄ / tetrahydrofuran; aq. ethanol / 1 h / -5 °C

3: 79 percent / DMAP / CH₂Cl₂; pyridine / 2 h / Ambient temperature

With dmap; sodium tetrahydroborate; Dess-Martin periodane; In tetrahydrofuran; pyridine; ethanol; dichloromethane;

DOI:10.1080/15257779508010720

upstream raw materials:

acetic anhydride

N-[9-((2R,3S,3aS,9aR)-3-Hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl]-2-phenoxy-acetamide

N²-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine

Downstream raw materials:

9-(2-O-acetyl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine

9-(2-O-acetyl-5-O-monomethoxytrityl-β-D-arabinofuranosyl)-N²-phenoxyacetylguanine