(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:1275611-55-6
Molecular Formula:C₅₈H₅₆N₇O₉P
Molecular Weight:1026.1
Hs Code.:

(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Synonyms:(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

There total 6 articles about (1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-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: 82.0%

: 1275611-02-3
(1R,3R,4R,7S)-1-(4,4'-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

: 124482-92-4,89992-70-1
2-cyanoethyl-N,N-(diisopropylamino)chlorophosphine

: 1275611-55-6
(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 2.5h; Inert atmosphere;
DOI:10.1021/jo500614a

Reference yield:

: 1202937-24-3
(1R,3R,4R,7S)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

: 1275611-55-6
(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

2: sodium L-ascorbate; copper(II) sulfate / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

With tetrabutyl ammonium fluoride; copper(II) sulfate; sodium L-ascorbate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol; 2: |Huisgen Cycloaddition;
DOI:10.1021/jo500614a

Reference yield:

: 1202937-22-1
(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-3-(5-iodoracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

: 1275611-55-6
(1R,3R,4R,7S)-7-[2-cyanoethoxy(diisopropylamino)phosphinoxy]-1-(4,4'-dimethoxytrityloxymethyl)-3-[5-(1-(1-pyrenyl)-1H-1,2,3-triazol-4-yl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine / 16 h / 20 °C / Inert atmosphere

2: tetrakis(triphenylphosphine) palladium⁽⁰⁾; copper(l) iodide; triethylamine / N,N-dimethyl-formamide / 12 h / 20 °C / Inert atmosphere; Darkness

3: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

4: sodium L-ascorbate; copper(II) sulfate / tetrahydrofuran; water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

5: N-ethyl-N,N-diisopropylamine / dichloromethane / 2.5 h / 20 °C / Inert atmosphere

With pyridine; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tetrabutyl ammonium fluoride; copper(II) sulfate; sodium L-ascorbate; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 2: |Sonogashira Cross-Coupling / 4: |Huisgen Cycloaddition;
DOI:10.1021/jo500614a