(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Base Information

• Chemical Name: (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 1067885-80-6
• Molecular Formula: C₂₇H₂₁F₃N₆O₆
• Molecular Weight: 582.496

Synonyms:(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property of (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

There total 9 articles about (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[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: 83.0%

sodium benzoate (532-32-1) + (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-hydroxy-1-methanesulfonyloxymethyl-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-78-2) → (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-80-6)

Guidance literature:

With 15-crown-5; In N,N-dimethyl-formamide; at 90 ℃;

DOI:10.1080/15257770701539153

Reference yield:

9-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-α-L-threo-pentofuranosyl]-6-N-benzoyladenine (410076-94-7) → (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-80-6)

Guidance literature:

Multi-step reaction with 7 steps

1: guanidine nitrate; sodium methylate / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2: pyridine / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

3: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 50 °C / Inert atmosphere

4: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 21 h / 20 °C / Cooling with ice; Inert atmosphere

5: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

6: boron trichloride / 1,2-dichloro-ethane; dichloromethane; hexane / 17 h / -78 - 20 °C / Inert atmosphere

7: 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 90 °C / Inert atmosphere

With pyridine; sodium azide; 15-crown-5; sodium methylate; guanidine nitrate; boron trichloride; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo4022937

Reference yield:

N-benzoyladenine (4005-49-6) → (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-benzoyloxymethyl-7-hydroxy-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-80-6)

Guidance literature:

Multi-step reaction with 8 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / 1,2-dichloro-ethane / Reflux; Inert atmosphere

1.2: 70 h / Reflux

1.3: Inert atmosphere

2.1: guanidine nitrate; sodium methylate / methanol; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

3.1: pyridine / dichloromethane / 3 h / -78 - 20 °C / Inert atmosphere

4.1: sodium azide; 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 50 °C / Inert atmosphere

5.1: sodium hydroxide; trimethylphosphane / water; tetrahydrofuran / 21 h / 20 °C / Cooling with ice; Inert atmosphere

6.1: pyridine / dichloromethane / 2 h / 0 °C / Inert atmosphere

7.1: boron trichloride / 1,2-dichloro-ethane; dichloromethane; hexane / 17 h / -78 - 20 °C / Inert atmosphere

8.1: 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 90 °C / Inert atmosphere

With pyridine; sodium azide; N,O-bis-(trimethylsilyl)-acetamide; 15-crown-5; sodium methylate; guanidine nitrate; boron trichloride; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: |Vorbrueggen Nucleoside Synthesis;

DOI:10.1021/jo4022937

upstream raw materials:

sodium benzoate

(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-hydroxy-1-methanesulfonyloxymethyl-5-trifluoroacetyl-2-oxa-5-azabicyclo[2.2.1]heptane

9-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-α-L-threo-pentofuranosyl]-6-N-benzoyladenine

9-(3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-α-L-threo-pentofuranosyl)-6-N-benzoyladenine

Downstream raw materials:

(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-hydroxy-1-hydroxymethyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-5-(pyren-1-yl)methyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-5-(pyren-1-yl)carbonyl-2-oxa-5-azabicyclo[2.2.1]heptane

(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)methyl-2-oxa-5-azabicyclo[2.2.1]heptane

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