(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Base Information

Chemical Name:(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)
CAS No.:226214-58-0
Molecular Formula:C₄₂H₅₁N₄O₉P
Molecular Weight:786.862
Hs Code.:

Synonyms:(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Suppliers and Price of (1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

There total 16 articles about (1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite) 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: 77.0%

: 226214-56-8
(1S,3R,4R, 8S)-8-hydoxy-1-(4,4’-dimethoxytrityloxymethyl)-3 (thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

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

: 226214-58-0
(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 6h; Inert atmosphere;

Reference yield:

: 22423-26-3
O-2,2'-cyclo-5-methyluridine

: 226214-58-0
(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Guidance literature:: Multi-step reaction with 15 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: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C / Inert atmosphere

With pyridine; 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; N-ethyl-N,N-diisopropylamine; sodium iodide; sodium hydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; acetone; toluene; mineral oil; benzene;

Reference yield:

: 1426833-56-8
1-[5-O-(4-methoxytrityl)-2-deoxy-2-iodo-3-(dimethyl)vinylsilyl-β-D-ribo-pentofuranosyl]-thymine

: 226214-58-0
(1S,3R,4R,8S)-1-(4,4’-dimethoxytrityloxymethyl)-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane8-O-(2-cyanoethyl-N,N-diisopropylphosphoroamidite)

Guidance literature:: Multi-step reaction with 12 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: N-ethyl-N,N-diisopropylamine / dichloromethane / 6 h / 20 °C / Inert atmosphere

With pyridine; 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; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; pyridine; methanol; dichloromethane; water; ethyl acetate; mineral oil; benzene;