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

Base Information

• Chemical Name: (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane
• CAS No.: 293751-16-3
• Molecular Formula: C₁₈H₁₉N₅O₅
• Molecular Weight: 385.379
• Mol file: 293751-16-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 10 articles about (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[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:

(1R,3R,4R,7S)-3-(guanin-9-yl)-7-benzyloxy-1-benzoyloxymethyl-2,5-dioxabicyclo-[2.2.1]heptane (709641-77-0) → (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-16-3)

Guidance literature:

With ammonia; In methanol; at 20 ℃; for 18h; Sealed tube;

DOI:10.1016/j.bmcl.2014.04.050

Reference yield:

(1R,3R,4R,7S)-7-benzyloxy-1-methanesulfonyloxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-15-2) → (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-16-3)

Guidance literature:

With sodium hydroxide; water; for 12h; Heating / reflux;

Reference yield:

3-O-benzyl-1,2-O-isopropylidene-α-D-ribo-pentodialdofuranose → (1S,3R,4R,7S)-7-benzyloxy-1-hydroxymethyl-3-(guanin-9-yl)-2,5-dioxabicyclo[2.2.1]heptane (293751-16-3)

Guidance literature:

Multi-step reaction with 7 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

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

DOI:10.1016/j.bmcl.2014.04.050

upstream raw materials:

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

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

3-O-benzyl-4-C-methanesulfonoxymethyl-5-methanesulfonyl-1,2-O-isopropylidene-α-D-erythro-pentofuranose

1,2-di-O-acetyl-3-O-benzyl-4-C-methanesulfonyloxymethyl-5-O-methanesulfonyl-D-erythro-pentofuranose

Downstream 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

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