(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

Base Information

Chemical Name:(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane
CAS No.:1426833-67-1
Molecular Formula:C₁₉H₂₂N₂O₆
Molecular Weight:374.393
Hs Code.:

Synonyms:(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

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Chemical Property of (1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

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Technology Process of (1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

There total 14 articles about (1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-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: 77.0%

: 1426833-68-2
(1R,3R,4R, 8S)-1-benzoyloxymethyl-8-benzyloxy-3-(thymin-1-yl)-2,6-dioxabicyclo[3,2,1]octane

: 1426833-67-1
(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

Guidance literature:: With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 1.5h; Reagent/catalyst; Time; Temperature; Concentration;

Reference yield:

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

: 1426833-67-1
(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

Guidance literature:: Multi-step reaction with 13 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

With pyridine; hydrogenchloride; dmap; 2,2'-azobis(isobutyronitrile); p-toluenesulfonic acid monohydrate; tetrabutyl ammonium fluoride; hexamethyldistannane; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; triethylamine; sodium iodide; sodium hydroxide; In tetrahydrofuran; pyridine; 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

: 1426833-67-1
(1S,3R,4R,8S)-8-benzyloxyoxy-1-hydroxymethyl-3-(thymin-yl)-2,6-dioxabicyclo[3,2,1]octane

Guidance literature:: Multi-step reaction with 10 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

With pyridine; hydrogenchloride; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hexamethyldistannane; sodium hydride; Dess-Martin periodane; ozone; methanesulfonyl chloride; sodium hydroxide; In tetrahydrofuran; pyridine; dichloromethane; water; ethyl acetate; mineral oil; benzene;