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

Base Information

• Chemical Name: 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
• CAS No.: 1610605-69-0
• Molecular Formula: C₂₅H₂₃N₅O₆
• Molecular Weight: 489.488
• Mol file: 1610605-69-0.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 13 articles about 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 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: 89.0%

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) → 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 (1610605-69-0)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; 1,4-dioxane; at 0 - 20 ℃; for 3h; Inert atmosphere;

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-((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 (1610605-69-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: pyridine / 18 h / 20 °C

3: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; dmap; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

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) → 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 (1610605-69-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 18 h / 20 °C

2: hydrogenchloride / 1,4-dioxane; tetrahydrofuran / 3 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydrogenchloride; In tetrahydrofuran; 1,4-dioxane;

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

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

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

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

Downstream raw materials:

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

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

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