(1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane
• CAS No.: 1301628-69-2
• Molecular Formula: C₃₆H₃₇N₅O₇
• Molecular Weight: 651.719

Synonyms:(1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane

There total 8 articles about (1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane 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: 80.0%

(1R,3R,4R,5R,7S)-3-(N2-acetylguanin-9-yl)-7-hydroxy-1-hydroxymethyl-5-methyl-2-oxabicylco[2.2.1]heptane (1301628-68-1) + 4,4'-dimethoxytrityl chloride (40615-36-9) → (1R,3R,4R,5R,7S)-3-(N2-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-69-2)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1021/jo200073q

Reference yield:

4-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose (945382-92-3) → (1R,3R,4R,5R,7S)-3-(N2-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-69-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: trifluorormethanesulfonic acid; acetic acid / dichloromethane / 0.5 h / 0 °C

2.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / 80 °C / Inert atmosphere

2.2: 1 h / 80 °C / Inert atmosphere

3.1: water; sodium hydroxide / tetrahydrofuran / 0 °C

4.1: 1-methyl-1H-imidazole / dichloromethane / 0 - 20 °C

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 90 °C / Inert atmosphere

6.1: acetic acid / 20 - 55 °C

7.1: 20% palladium(II) hydroxide on carbon; formic acid / methanol / 2.5 h / Inert atmosphere; Reflux

8.1: pyridine / 20 °C

With pyridine; 1-methyl-1H-imidazole; formic acid; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); trifluorormethanesulfonic acid; 20% palladium(II) hydroxide on carbon; water; tri-n-butyl-tin hydride; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo200073q

Reference yield:

C26H30O7 (945382-94-5) → (1R,3R,4R,5R,7S)-3-(N2-acetylguanin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-7-hydroxy-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-69-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 0.5 h / 80 °C / Inert atmosphere

1.2: 1 h / 80 °C / Inert atmosphere

2.1: water; sodium hydroxide / tetrahydrofuran / 0 °C

3.1: 1-methyl-1H-imidazole / dichloromethane / 0 - 20 °C

4.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 2 h / 90 °C / Inert atmosphere

5.1: acetic acid / 20 - 55 °C

6.1: 20% palladium(II) hydroxide on carbon; formic acid / methanol / 2.5 h / Inert atmosphere; Reflux

7.1: pyridine / 20 °C

With pyridine; 1-methyl-1H-imidazole; formic acid; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); 20% palladium(II) hydroxide on carbon; water; tri-n-butyl-tin hydride; acetic acid; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; toluene;

DOI:10.1021/jo200073q

upstream raw materials:

4-C-allyl-3,5-di-O-benzyl-1,2-O-isopropylidene-α-D-ribofuranose

C₂₆H₃₀O₇

9-[4-C-allyl-3,5-di-O-benzyl-2-O-acetyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

9-[4-C-allyl-3,5-di-O-benzyl-β-D-ribofuranosyl]-N2-acetyl-O6-diphenylcarbamoylguanine

Downstream raw materials:

(1R,3R,4R,5R,7S)-3-(N₂-acetylguanin-9-yl)-7-(2-cyanoethoxydiisopropylaminophosphinoxy)-1-(4,4'-dimethoxytrityloxy)methyl-5-methyl-2-oxabicyclo[2.2.1]heptane

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