(4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid

Base Information

• Chemical Name: (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid
• CAS No.: 312710-02-4
• Molecular Formula: C₆₇H₇₄N₆O₁₇Si
• Molecular Weight: 1263.44
• Mol file: 312710-02-4.mol

Synonyms:(4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid

Chemical Property of (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid

There total 11 articles about (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid 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: 49.0%

2,2'-[1,4-phenylenebis(oxy)]bisacetic acid (2245-53-6) + 5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}-N6-{{{2-[(triisopropyl)oxy]benzyl}oxy}carbonyl}adenosine (312710-01-3) → (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid (312710-02-4)

Guidance literature:

With dmap; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In pyridine; at 20 ℃; for 0.5h;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

triisopropylsilyl chloride (13154-24-0) → (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid (312710-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / NaH / dimethylformamide / 0.5 h / -70 °C

2: Et₃N / pyridine; CH₂Cl₂; toluene / 18 h / 20 °C

3: NaOH / tetrahydrofuran; H₂O; methanol / 0.08 h / 4 °C

4: 49 percent / BOP; iPr₂NEt; DMAP / pyridine / 0.5 h / 20 °C

With dmap; sodium hydroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Condensation / 3: Hydrolysis / 4: Esterification;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

Reference yield:

salicylic alcohol (90-01-7) → (4-{(2R,3R,4R,5R)-2-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-[(S)-1-(2-nitro-phenyl)-ethoxymethoxy]-5-[6-(2-triisopropylsilanyloxy-benzyloxycarbonylamino)-purin-9-yl]-tetrahydro-furan-3-yloxycarbonylmethoxy}-phenoxy)-acetic acid (312710-02-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / NaH / dimethylformamide / 0.5 h / -70 °C

2: Et₃N / pyridine; CH₂Cl₂; toluene / 18 h / 20 °C

3: NaOH / tetrahydrofuran; H₂O; methanol / 0.08 h / 4 °C

4: 49 percent / BOP; iPr₂NEt; DMAP / pyridine / 0.5 h / 20 °C

With dmap; sodium hydroxide; sodium hydride; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Condensation / 2: Condensation / 3: Hydrolysis / 4: Esterification;

DOI:10.1002/1522-2675(20000906)83:9<2477::AID-HLCA2477>3.0.CO;2-9

upstream raw materials:

2,2'-[1,4-phenylenebis(oxy)]bisacetic acid

5'-O-(4,4'-dimethoxytrityl)-2'-O-{[(S)-1-(2-nitrophenyl)ethoxy]methyl}-N⁶-{{{2-[(triisopropyl)oxy]benzyl}oxy}carbonyl}adenosine

triisopropylsilyl chloride

salicylic alcohol