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

Base Information

Chemical Name:(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane
CAS No.:1275611-15-8
Molecular Formula:C₃₆H₃₈N₂O₈Si
Molecular Weight:654.792
Hs Code.:

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

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Chemical Property of (1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

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Technology Process of (1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

There total 11 articles about (1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)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:

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

: 1275611-15-8
(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 12 steps

1.1: N,O-bis-(trimethylsilyl)-acetamide / acetonitrile / Reflux; Inert atmosphere

1.2: 28 h / 20 °C / Reflux; Inert atmosphere

2.1: hydrogenchloride / methanol / 24 h / 20 °C

3.1: pyridine / 4 h / 20 °C / Inert atmosphere

4.1: sodium hydroxide; water / 1,4-dioxane / 4 h / 20 °C

5.1: N,N-dimethyl-formamide / 20 h / 90 °C / Inert atmosphere

6.1: ammonia / methanol / 14 h / 20 °C

7.1: formic acid / 20 wt% Pd(OH)2/C / water; tetrahydrofuran; methanol / 24 h / Reflux

8.1: pyridine / 14 h / 60 °C

9.1: iodine; ammonium cerium (IV) nitrate; acetic acid / 0.83 h / 80 °C

10.1: ammonia / methanol / 12 h / 20 °C / Sealed tube

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

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

With pyridine; hydrogenchloride; formic acid; N,O-bis-(trimethylsilyl)-acetamide; ammonium cerium (IV) nitrate; ammonia; water; iodine; acetic acid; triethylamine; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 20 wt% Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; acetonitrile; 12.1: Sonogashira Coupling;

Reference yield:

: 1275611-05-6
1-[2-O-acetyl-3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

: 1275611-15-8
(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 11 steps

1: hydrogenchloride / methanol / 24 h / 20 °C

2: pyridine / 4 h / 20 °C / Inert atmosphere

3: sodium hydroxide; water / 1,4-dioxane / 4 h / 20 °C

4: N,N-dimethyl-formamide / 20 h / 90 °C / Inert atmosphere

5: ammonia / methanol / 14 h / 20 °C

6: formic acid / 20 wt% Pd(OH)2/C / water; tetrahydrofuran; methanol / 24 h / Reflux

7: pyridine / 14 h / 60 °C

8: iodine; ammonium cerium (IV) nitrate; acetic acid / 0.83 h / 80 °C

9: ammonia / methanol / 12 h / 20 °C / Sealed tube

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

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

With pyridine; hydrogenchloride; formic acid; ammonium cerium (IV) nitrate; ammonia; water; iodine; acetic acid; triethylamine; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 20 wt% Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; 11: Sonogashira Coupling;

Reference yield:

: 1275611-06-7
1-[3-O-benzyl-5-O-(methanesulfonyl)-4-C-(methanesulfonyloxymethyl)-α-L-threo-pentofuranosyl]uracil

: 1275611-15-8
(1S,3R,4S,7R)-1-(4,4′-dimethoxytrityloxymethyl)-7-hydroxy-3-[5-(trimethylsilylethynyl)uracil-1-yl]-2,5-dioxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 10 steps

1: pyridine / 4 h / 20 °C / Inert atmosphere

2: sodium hydroxide; water / 1,4-dioxane / 4 h / 20 °C

3: N,N-dimethyl-formamide / 20 h / 90 °C / Inert atmosphere

4: ammonia / methanol / 14 h / 20 °C

5: formic acid / 20 wt% Pd(OH)2/C / water; tetrahydrofuran; methanol / 24 h / Reflux

6: pyridine / 14 h / 60 °C

7: iodine; ammonium cerium (IV) nitrate; acetic acid / 0.83 h / 80 °C

8: ammonia / methanol / 12 h / 20 °C / Sealed tube

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

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

With pyridine; formic acid; ammonium cerium (IV) nitrate; ammonia; water; iodine; acetic acid; triethylamine; sodium hydroxide; copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; 20 wt% Pd(OH)2/C; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide; 10: Sonogashira Coupling;