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

Base Information

• Chemical Name: (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)carbonyl-2-oxa-5-azabicyclo[2.2.1]heptane
• CAS No.: 1067885-87-3
• Molecular Formula: C₆₅H₆₁N₈O₈P
• Molecular Weight: 1113.22
• Mol file: 1067885-87-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)carbonyl-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: 67.0%

(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 (1067885-86-2) + 2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine (124482-92-4,89992-70-1) → (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)carbonyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-87-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 20 ℃;

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)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)carbonyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-87-3)

Guidance literature:

Multi-step reaction with 11 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

8: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 °C / Inert atmosphere

9: pyridine / 23 h / 20 °C / Cooling with ice; Inert atmosphere

10: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane; dichloromethane / 45 h / 20 °C / Inert atmosphere

11: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane; dichloromethane / 22 h / 20 °C / Inert atmosphere

With pyridine; sodium azide; 15-crown-5; sodium methylate; guanidine nitrate; boron trichloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo4022937

Reference yield:

9-(3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-α-L-threo-pentofuranosyl)-6-N-benzoyladenine (410076-95-8) → (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-[2-cyanoethoxy-(diisopropylamino)phosphinoxy]-1-(4,4′-dimethoxytrityloxymethyl)-5-(pyren-1-yl)carbonyl-2-oxa-5-azabicyclo[2.2.1]heptane (1067885-87-3)

Guidance literature:

Multi-step reaction with 10 steps

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

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

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

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

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

6: 15-crown-5 / N,N-dimethyl-formamide / 23 h / 20 - 90 °C / Inert atmosphere

7: sodium hydroxide / water; 1,4-dioxane / 2 h / 0 °C / Inert atmosphere

8: pyridine / 23 h / 20 °C / Cooling with ice; Inert atmosphere

9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / 1,2-dichloro-ethane; dichloromethane / 45 h / 20 °C / Inert atmosphere

10: N-ethyl-N,N-diisopropylamine / 1,2-dichloro-ethane; dichloromethane / 22 h / 20 °C / Inert atmosphere

With pyridine; sodium azide; 15-crown-5; boron trichloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1021/jo4022937

upstream raw materials:

(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

2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

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

Refernces

• 1、 Andersen, Nicolai K.,Wengel, Jesper,Hrdlicka, Patrick J.. "N2′-functionalized 2′-amino-α-L-LNA adenine derivatives - Efficient targeting of single stranded DNA". . p. 1415 - 1417. Retrieved 2008/09/20.