(1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane
• CAS No.: 1301628-57-8
• Molecular Formula: C₂₀H₂₁N₅O₄
• Molecular Weight: 395.418

Synonyms:(1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane

Chemical Property of (1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-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-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane

There total 8 articles about (1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-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: 52.0%

(1R,3R,4R,5R,7S)-3-(adenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-56-7) + benzoyl chloride (98-88-4) → (1R,3R,4R,5R,7S)-3-(N6-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-57-8)

Guidance literature:

(1R,3R,4R,5R,7S)-3-(adenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane; With pyridine; chloro-trimethyl-silane; at 0 ℃; for 1.25h;

benzoyl chloride; With pyridine; at 20 ℃; for 2h;

With ammonia; water; In pyridine; at 0 - 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-(N6-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-57-8)

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 / acetonitrile / 0.75 h / Reflux

2.2: 0 - 50 °C

3.1: water; sodium hydroxide / tetrahydrofuran / 0 - 20 °C

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

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

6.1: methanol; ammonia / 16 h / 20 °C

7.1: 20% palladium(II) hydroxide on carbon; ammonium formate / methanol / 16 h / 60 °C

8.1: pyridine; chloro-trimethyl-silane / 1.25 h / 0 °C

8.2: 2 h / 20 °C

8.3: 0 - 20 °C

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

DOI:10.1021/jo200073q

Reference yield:

C26H30O7 (945382-94-5) → (1R,3R,4R,5R,7S)-3-(N6-benzoyladenin-9-yl)-7-hydroxy-1-(hydroxymethyl)-5-methyl-2-oxabicyclo[2.2.1]heptane (1301628-57-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / 0.75 h / Reflux

1.2: 0 - 50 °C

2.1: water; sodium hydroxide / tetrahydrofuran / 0 - 20 °C

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

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

5.1: methanol; ammonia / 16 h / 20 °C

6.1: 20% palladium(II) hydroxide on carbon; ammonium formate / methanol / 16 h / 60 °C

7.1: pyridine; chloro-trimethyl-silane / 1.25 h / 0 °C

7.2: 2 h / 20 °C

7.3: 0 - 20 °C

With pyridine; 1-methyl-1H-imidazole; methanol; chloro-trimethyl-silane; N,O-bis-(trimethylsilyl)-acetamide; 2,2'-azobis(isobutyronitrile); 20% palladium(II) hydroxide on carbon; ammonia; water; tri-n-butyl-tin hydride; ammonium formate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; toluene; acetonitrile;

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-β-D-ribofuranosyl]-N6-benzoyladenine

9-[4-C-allyl-3,5-di-O-benzyl-2-O-phenoxythiocarbonyl-β-D-ribofuranosyl]-N6-benzoyladenine

Downstream raw materials:

(1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-7-(2-cyanoethoxydiisopropylaminophosphinoxy)-1-(4,4'-dimethoxytrityloxy)methyl-5-methyl-2-oxabicyclo[2.2.1]heptane

(1R,3R,4R,5R,7S)-3-(N₆-benzoyladenin-9-yl)-1-(4,4'-dimethoxytrityoxy)methyl-5-methyl-7-hydroxy-2-oxabicyclo[2.2.1]heptane

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