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

Base Information

Chemical Name:(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]heptane
CAS No.:1067885-82-8
Molecular Formula:C₃₉H₃₆N₆O₆
Molecular Weight:684.751
Hs Code.:

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

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

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

There total 10 articles about (1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-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: 38.0%

: 1067885-81-7
(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-7-hydroxy-1-hydroxymethyl-2-oxa-5-azabicyclo[2.2.1]heptane

: 40615-36-9
4,4'-dimethoxytrityl chloride

: 1067885-82-8
(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]heptane

: 1513633-26-5
(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-5-(4,4′-dimethoxytrityl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: With pyridine; at 20 ℃; for 23h; Cooling with ice; Inert atmosphere;
DOI:10.1021/jo4022937

Reference yield:

: 410076-95-8
9-(3-O-benzyl-5-O-(methanesulfonyl)-4-C-[[(methanesulfonyl)oxy]methyl]-α-L-threo-pentofuranosyl)-6-N-benzoyladenine

: 1067885-82-8
(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 8 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

With pyridine; sodium azide; 15-crown-5; boron trichloride; sodium hydroxide; trimethylphosphane; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide;
DOI:10.1021/jo4022937

Reference yield:

: 410076-93-6
3-O-benzyl-1,2-di-O-acetyl-5-O-(methylsulfonyl)-4-C-(methylsulfonyloxymethyl)-α,β-L-threo-pentofuranose

: 1067885-82-8
(1S,3R,4S,7R)-3-(6-N-benzoyladenin-9-yl)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-2-oxa-5-azabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 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

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

10.1: pyridine / 23 h / 20 °C / Cooling with ice; 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; 1,4-dioxane; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: |Vorbrueggen Nucleoside Synthesis;
DOI:10.1021/jo4022937