(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Base Information

Chemical Name:(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane
CAS No.:1092803-45-6
Molecular Formula:C₂₈H₃₂N₂O₅Si
Molecular Weight:504.658
Hs Code.:

Synonyms:(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

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Chemical Property of (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

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Technology Process of (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

There total 13 articles about (1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[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: 62.0%

: 1092803-44-5
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-(2-naphthylmethoxy)-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

: 1092803-45-6
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 20 ℃; for 6h;

Reference yield:

: 956485-06-6
3-O-(2-naphthylmethyl)-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

: 1092803-45-6
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 18 steps

1.1: water; acetic acid / 16 h / 20 °C

2.1: sodium periodate / 1,4-dioxane; water / 1.67 h

3.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

4.1: triethylamine / dichloromethane; methanol / 18 h / 0 - 20 °C

5.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

6.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C

6.2: 16.33 h / -78 - 20 °C

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

7.2: 4 h / 50 °C

8.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

8.2: 0.5 h

9.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

9.2: 2 h / -78 °C

10.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

11.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C

12.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

13.1: sulfuric acid / 0.25 h / 20 °C

14.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / Cooling with ice; Reflux

15.1: ammonia / methanol / 16 h / 20 °C

16.1: dmap / acetonitrile / 1 h / 0 °C

17.1: tri-n-butyl-tin hydride / toluene / 0.5 h / Reflux

17.2: 3.5 h / Reflux

18.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

With dmap; sodium periodate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; water; tri-n-butyl-tin hydride; sodium hydride; acetic acid; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 14.1: Vorbrugen reaction;

Reference yield:

: 1091607-89-4
(R)-1-((3aR,5R,6R,6aR)-2,2-dimethyl-6-(naphthalen-2-ylmethoxy)tetrahydrofuro[3,2-d][1,3]dioxol-5-yl)ethane-1,2-diol

: 1092803-45-6
(1R,3R,4R,7S)-1-(tert-butyldiphenylsilyloxymethyl)-5-methylene-7-hydroxy-3-(uracil-1-yl)-2-oxabicyclo[2.2.1]heptane

Guidance literature:: Multi-step reaction with 17 steps

1.1: sodium periodate / 1,4-dioxane; water / 1.67 h

2.1: sodium hydroxide / water; tetrahydrofuran / 72 h / 20 °C / Cooling with ice

3.1: triethylamine / dichloromethane; methanol / 18 h / 0 - 20 °C

4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

5.1: n-butyllithium / tetrahydrofuran / 2 h / 0 °C

5.2: 16.33 h / -78 - 20 °C

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 24 h / 20 °C

6.2: 4 h / 50 °C

7.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

7.2: 0.5 h

8.1: triphenylphosphine / dichloromethane / 0.5 h / 0 °C

8.2: 2 h / -78 °C

9.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

10.1: tetrahydrofuran; hexanes / 0.5 h / -78 °C

11.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 20 °C

12.1: sulfuric acid / 0.25 h / 20 °C

13.1: N,O-bis-(trimethylsilyl)-acetamide; trimethylsilyl trifluoromethanesulfonate / acetonitrile / 2 h / Cooling with ice; Reflux

14.1: ammonia / methanol / 16 h / 20 °C

15.1: dmap / acetonitrile / 1 h / 0 °C

16.1: tri-n-butyl-tin hydride / toluene / 0.5 h / Reflux

16.2: 3.5 h / Reflux

17.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone; water / dichloromethane / 6 h / 20 °C

With dmap; sodium periodate; n-butyllithium; N,O-bis-(trimethylsilyl)-acetamide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; sulfuric acid; ammonia; water; tri-n-butyl-tin hydride; sodium hydride; dimethyl sulfoxide; triethylamine; 9-bora-bicyclo[3.3.1]nonane; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; hexanes; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; mineral oil; 13.1: Vorbrugen reaction;