N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Base Information

• Chemical Name: N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide
• CAS No.: 1610605-78-1
• Molecular Formula: C₃₁H₃₇N₅O₆Si
• Molecular Weight: 603.75
• Mol file: 1610605-78-1.mol

Synonyms:N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Chemical Property of N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

There total 12 articles about N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide 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: 60.0%

2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one (1610605-77-0) + benzoyl chloride (98-88-4) → N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide (1610605-78-1)

Guidance literature:

With pyridine; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

(1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-16-3) → N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide (1610605-78-1)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap / dichloromethane; pyridine / 72 h / 20 °C

2: pyridine / 18 h / 20 °C

With pyridine; dmap; In pyridine; dichloromethane;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose → N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide (1610605-78-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: sodium hydroxide / water; 1,4-dioxane / 144 h / 0 - 20 °C

2.1: pyridine / 1 h / 20 °C

3.1: sulfuric acid / acetic acid / 20 °C

4.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / 1 h / Reflux

4.2: 3 h / Reflux; Inert atmosphere

5.1: 3-Hydroxypropionitrile; sodium hydride / mineral oil; tetrahydrofuran / 18 h / 0 - 20 °C

6.1: dimethyl sulfoxide / 5 h / 100 °C

7.1: ammonia / methanol / 18 h / 20 °C / Sealed tube

8.1: dmap / dichloromethane; pyridine / 72 h / 20 °C

9.1: pyridine / 18 h / 20 °C

With pyridine; dmap; N,O-bis-(trimethylsilyl)-acetamide; sulfuric acid; ammonia; sodium hydride; 3-Hydroxypropionitrile; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; dichloromethane; water; acetic acid; dimethyl sulfoxide; 1,2-dichloro-ethane; mineral oil;

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(((tert-butyldimethylsilyl)oxy)methyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

benzoyl chloride

(1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane

1,2-O-isopropylidene-3-O-benzyl-4-hydroxymethyl-α-D-ribofuranose

Downstream raw materials:

N-(9-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

N-(9-((1R,3R,4R,7S)-7-(benzyloxy)-1-((S)-1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-6-oxo-6,9-dihydro-1H-purin-2-yl)benzamide

2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one

2-amino-9-((1R,3R,4R,7S)-7-(benzyloxy)-1-(1-hydroxyethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)-1H-purin-6(9H)-one