N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)

Base Information

• Chemical Name: N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)
• CAS No.: 457880-69-2
• Molecular Formula: C₄₆H₄₆N₆O₁₂
• Molecular Weight: 874.904

Synonyms:N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)

Chemical Property of N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

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Technology Process of N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate)

There total 11 articles about N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate) 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: 55.0%

bis(4-nitrophenyl) heptane-1,7-dioate (49761-23-1) + N2-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine (457880-59-0) → N2-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate) (457880-69-2)

Guidance literature:

With dmap; N-ethyl-N,N-diisopropylamine; In pyridine; at 25 ℃; for 14h;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

Reference yield:

benzyl 3-deoxy-α-D-xylopyranoside (112482-91-4) → N2-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate) (457880-69-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 9.5 g / iPr₂NEt; AgNO₃ / CH₂Cl₂ / -78 - 25 °C

2.1: H₂ / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr

3.1: 16.0 g / pyridine / 25 °C

4.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C

4.2: Et₃SiOTf / benzene / 1.5 h / 45 °C

5.1: 9.13 g / Et₄NF*2H₂O; AcOH / acetonitrile / 0.33 h / 25 °C

6.1: AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

7.1: NaNO₂ / dimethylsulfoxide / 4 h / 75 °C

8.1: 2.17 g / NaOH; water / tetrahydrofuran; methanol / 0.13 h / 4 °C

9.1: 55 percent / iPr₂NEt; DMAP / pyridine / 14 h / 25 °C

With pyridine; dmap; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; water; hydrogen; tetraethylammonium fluoride; silver nitrate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium nitrite; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

Reference yield:

benzyl 4-O-[(tert-butyl)dimethylsilyl]-3-deoxy-α-D-ribopyranoside (457880-53-4) → N2-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine 2'-(4-nitrophenyl heptanedioate) (457880-69-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: H₂ / Pd(OH)2/C / ethanol / 48 h / 25 °C / 4500.36 Torr

2.1: 16.0 g / pyridine / 25 °C

3.1: N,O-bis(trimethylsilyl)acetamide / 1,2-dichloro-ethane / 0.75 h / 60 °C

3.2: Et₃SiOTf / benzene / 1.5 h / 45 °C

4.1: 9.13 g / Et₄NF*2H₂O; AcOH / acetonitrile / 0.33 h / 25 °C

5.1: AgNO₃ / CH₂Cl₂ / 0.5 h / 25 °C

6.1: NaNO₂ / dimethylsulfoxide / 4 h / 75 °C

7.1: 2.17 g / NaOH; water / tetrahydrofuran; methanol / 0.13 h / 4 °C

8.1: 55 percent / iPr₂NEt; DMAP / pyridine / 14 h / 25 °C

With pyridine; dmap; sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; water; hydrogen; tetraethylammonium fluoride; silver nitrate; acetic acid; N-ethyl-N,N-diisopropylamine; sodium nitrite; palladium dihydroxide; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; acetonitrile;

DOI:10.1002/1522-2675(200205)85:5<1443::AID-HLCA1443>3.0.CO;2-U

upstream raw materials:

bis(4-nitrophenyl) heptane-1,7-dioate

N²-acetyl-9-[3'-deoxy-4'-O-(4,4'-dimethoxytrityl)-β-D-ribopyranosyl]guanine

4,4'-dimethoxytrityl chloride

benzyl 3-deoxy-α-D-xylopyranoside

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