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

Base Information

• Chemical Name: 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
• CAS No.: 169886-61-7
• Molecular Formula: C₃₀H₄₅N₅O₈Si₂
• Molecular Weight: 659.887
• Mol file: 169886-61-7.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 2 articles about 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 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:

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 → 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)

Guidance literature:

With sodium tetrahydroborate; In tetrahydrofuran; ethanol; at -5 ℃; for 1h; Yield given;

DOI:10.1080/15257779508010720

Reference yield:

N2-phenoxyacetyl-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)guanosine (131474-72-1) → 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)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1080/15257779508010720

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

upstream raw materials:

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

Downstream raw materials:

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

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

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