(1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane

Base Information

• Chemical Name: (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane
• CAS No.: 1426833-70-6
• Molecular Formula: C₄₀H₃₉N₃O₈
• Molecular Weight: 689.765

Synonyms:(1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane

Chemical Property of (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane

There total 17 articles about (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane 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: 94.0%

(1S,3R,4R, 85)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-thymin-yl)-2,6-dioxabicyclo[3,2,1]octane (1426833-69-3) + benzoic acid anhydride (93-97-0) → (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane (1426833-70-6)

Guidance literature:

(1S,3R,4R, 85)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-thymin-yl)-2,6-dioxabicyclo[3,2,1]octane; With 1,2,4-Triazole; triethylamine; trichlorophosphate; In acetonitrile; at 0 - 20 ℃; for 4.83333h; Cooling with ice; Inert atmosphere;

With ammonia; In 1,4-dioxane; at 20 ℃; for 1h;

benzoic acid anhydride;

Reference yield:

O-2,2'-cyclo-5-methyluridine (22423-26-3) → (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane (1426833-70-6)

Guidance literature:

Multi-step reaction with 16 steps

1.1: p-toluenesulfonic acid monohydrate; sodium iodide / acetone / 4 h / 55 °C

2.1: pyridine / 20 °C / Inert atmosphere

3.1: triethylamine; dmap / toluene / 1.17 h / 20 °C / Inert atmosphere

4.1: 2,2'-azobis(isobutyronitrile); hexamethyldistannane / benzene / 5 h / Reflux

4.2: 1 h / 20 °C

5.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C / Inert atmosphere; Cooling with ice

5.2: 19 h / -10 - 4 °C

6.1: hydrogenchloride / ethyl acetate / 2 h / 0 °C / Cooling with ice

7.1: Dess-Martin periodane / dichloromethane / 2.5 h / 0 °C

7.2: 15 h

8.1: pyridine / 3 h / 20 °C / Inert atmosphere

9.1: ozone / dichloromethane / 1 h / -78 °C / Cooling with acetone-dry ice

9.2: 0.33 h / 0 - 20 °C

10.1: pyridine / 20 °C / Inert atmosphere

11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

12.1: pyridine; methanesulfonyl chloride / 20 °C / Inert atmosphere

12.2: 1.33 h / 20 - 60 °C

12.3: 5 h / 130 °C

13.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C

14.1: ammonium formate; 10 wt% Pd(OH)2 on carbon / methanol / 3 h / Reflux

14.2: Inert atmosphere

15.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

16.1: triethylamine; 1,2,4-Triazole; trichlorophosphate / acetonitrile / 4.83 h / 0 - 20 °C / Cooling with ice; Inert atmosphere

16.2: 1 h / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); 10 wt% Pd(OH)2 on carbon; p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; hexamethyldistannane; ammonium formate; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; sodium iodide; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; mineral oil; benzene;

Reference yield:

1-[5-O-(4-methoxytrityl)-2-deoxy-2-iodo-3-(dimethyl)vinylsilyl-β-D-ribo-pentofuranosyl]-thymine (1426833-56-8) → (1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane (1426833-70-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 2,2'-azobis(isobutyronitrile); hexamethyldistannane / benzene / 5 h / Reflux

1.2: 1 h / 20 °C

2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / -10 °C / Inert atmosphere; Cooling with ice

2.2: 19 h / -10 - 4 °C

3.1: hydrogenchloride / ethyl acetate / 2 h / 0 °C / Cooling with ice

4.1: Dess-Martin periodane / dichloromethane / 2.5 h / 0 °C

4.2: 15 h

5.1: pyridine / 3 h / 20 °C / Inert atmosphere

6.1: ozone / dichloromethane / 1 h / -78 °C / Cooling with acetone-dry ice

6.2: 0.33 h / 0 - 20 °C

7.1: pyridine / 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C / Inert atmosphere

9.1: pyridine; methanesulfonyl chloride / 20 °C / Inert atmosphere

9.2: 1.33 h / 20 - 60 °C

9.3: 5 h / 130 °C

10.1: sodium hydroxide / tetrahydrofuran; water / 1.5 h / 20 °C

11.1: ammonium formate; 10 wt% Pd(OH)2 on carbon / methanol / 3 h / Reflux

11.2: Inert atmosphere

12.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C / Inert atmosphere

13.1: triethylamine; 1,2,4-Triazole; trichlorophosphate / acetonitrile / 4.83 h / 0 - 20 °C / Cooling with ice; Inert atmosphere

13.2: 1 h / 20 °C

With pyridine; 1H-imidazole; 1,2,4-Triazole; hydrogenchloride; 2,2'-azobis(isobutyronitrile); 10 wt% Pd(OH)2 on carbon; tetrabutyl ammonium fluoride; hexamethyldistannane; ammonium formate; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; mineral oil; benzene;

upstream raw materials:

1-[5-O-(4-methoxytrityl)-2-deoxy-2-iodo-3-(dimethyl)vinylsilyl-β-D-ribo-pentofuranosyl]-thymine

1-[5-O-(4-methoxytrityl)-2-deoxy-2-iodo-β-D-ribofuranosyl] 5-methyluracil

1-[3-O-benzyl-2-deoxy-2-vinyl-β-D-ribo-pentofuranosyl]thymine

1-[3-O-benzyl-4-C-hydroxymethyl-2-deoxy-2-vinyl-3-β-ribo-pentofuranosyl]thymine

Downstream raw materials:

(1S,3R,4R,8S)-8-triethylsilyloxy-1-(4,4’-dimethoxytrityloxymethyl)-3-(N4-benzoyl-5-methylcytosin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

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