N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide

Base Information

• Chemical Name: N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide
• CAS No.: 166593-56-2
• Molecular Formula: C₂₅H₃₂N₆O₈
• Molecular Weight: 544.564
• Mol file: 166593-56-2.mol

Synonyms:N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide

Chemical Property of N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide

There total 6 articles about N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide 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-[6-[2-(4-Nitro-phenyl)-ethoxy]-9-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-propoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-yl]-isobutyramide (166593-48-2) → N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide (166593-56-2)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1016/S0040-4039(00)75987-9

Reference yield:

D-ribose (50-69-1) → N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide (166593-56-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 85 percent / HCl / 20 °C

2: 90 percent / pyridine / Ambient temperature

3: 1.) DMAP; 2.) PPh₃, Pd(OAc)2 / 1.) acetonitrile, RT; 2.) toluene, reflux

4: 92 percent / H₂ / 10 percent Pd/C / ethyl acetate / Ambient temperature

5: 75 percent / DBU / 1,2-dichloro-ethane / Ambient temperature

6: 86 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / Ambient temperature

7: 95 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

With pyridine; hydrogenchloride; dmap; palladium diacetate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)75987-9

Reference yield:

benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranoside (117363-13-0) → N-{9-((2R,3R,4R,5R)-4-Hydroxy-5-hydroxymethyl-3-propoxy-tetrahydro-furan-2-yl)-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide (166593-56-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) DMAP; 2.) PPh₃, Pd(OAc)2 / 1.) acetonitrile, RT; 2.) toluene, reflux

2: 92 percent / H₂ / 10 percent Pd/C / ethyl acetate / Ambient temperature

3: 75 percent / DBU / 1,2-dichloro-ethane / Ambient temperature

4: 86 percent / trimethylsilyl trifluoromethanesulfonate / 1,2-dichloro-ethane / Ambient temperature

5: 95 percent / Bu₄NF / tetrahydrofuran / Ambient temperature

With dmap; palladium diacetate; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; ethyl acetate; 1,2-dichloro-ethane;

DOI:10.1016/S0040-4039(00)75987-9

upstream raw materials:

N-[6-[2-(4-Nitro-phenyl)-ethoxy]-9-((2R,3R,3aR,9aR)-5,5,7,7-tetraisopropyl-3-propoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-9H-purin-2-yl]-isobutyramide

D-ribose

(2R,3R,3aR,9aR)-5,5,7,7-Tetraisopropyl-3-propoxy-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-ol

benzyl 3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-β-D-ribofuranoside

Downstream raw materials:

N-{9-{(2R,3R,4R,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-hydroxy-3-propoxy-tetrahydro-furan-2-yl}-6-[2-(4-nitro-phenyl)-ethoxy]-9H-purin-2-yl}-isobutyramide