[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

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Chemical Name:[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran
CAS No.:1582753-09-0
Molecular Formula:C₃₁H₄₁NO₄Si
Molecular Weight:519.756
Hs Code.:

Synonyms:[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

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Chemical Property of [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

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Technology Process of [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

There total 13 articles about [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran 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: 90.0%

: [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitrovinyl)tetrahydrofuran

: 1582753-09-0
[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

Guidance literature:: With sodium tetrahydroborate; ethanol; In 1,4-dioxane; at 0 - 20 ℃; for 7h; Inert atmosphere;
DOI:10.1021/ol500657f

Reference yield:

: 905589-27-7
(3S)-4-(tert-butyldiphenylsilyl)oxy-3-(triethylsilyl)oxy-butyraldehyde

: 1582753-09-0
[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 13 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; pyridine / tetrahydrofuran; dimethyl sulfoxide / 6 h / Inert atmosphere

3.1: trifluoroacetic acid / dichloromethane; methanol / 0.5 h / 0 °C

4.1: dirhodium tetraacetate / benzene / 0.08 h / Reflux; Inert atmosphere

5.1: tris(triphenylphosphine)rhodium(l) chloride; triphenylphosphine; isopropyl alcohol / 1,4-dioxane / 0.5 h / 60 °C / Inert atmosphere

6.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

6.2: 0.58 h / -78 - 20 °C / Inert atmosphere

7.1: methanol / benzene; hexane / 0.08 h / 0 °C / Inert atmosphere

8.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C / Inert atmosphere

9.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

10.1: N,N,N',N'-tetramethylguanidine / 10 h / Inert atmosphere

11.1: sulfuric acid / 2 h / 0 °C

12.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

13.1: sodium tetrahydroborate; ethanol / 1,4-dioxane / 7 h / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; dirhodium tetraacetate; sodium tetrahydroborate; tris(triphenylphosphine)rhodium(l) chloride; ethanol; sulfuric acid; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; isopropyl alcohol; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; N,N,N',N'-tetramethylguanidine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; benzene; 9.1: |Dess-Martin Oxidation;
DOI:10.1021/ol500657f

Reference yield:

: (R)-3-methylcyclohex-2-en-1-yl (5S)-6-(tert-butyldiphenylsilyl)oxy-2-diazo-5-(triethylsilyl)oxy-3-hydroxyhexanoate

: 1582753-09-0
[2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylene-2-(2-nitroethyl)tetrahydrofuran

Guidance literature:: Multi-step reaction with 12 steps

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; pyridine / tetrahydrofuran; dimethyl sulfoxide / 6 h / Inert atmosphere

2.1: trifluoroacetic acid / dichloromethane; methanol / 0.5 h / 0 °C

3.1: dirhodium tetraacetate / benzene / 0.08 h / Reflux; Inert atmosphere

4.1: tris(triphenylphosphine)rhodium(l) chloride; triphenylphosphine; isopropyl alcohol / 1,4-dioxane / 0.5 h / 60 °C / Inert atmosphere

5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.08 h / -78 °C / Inert atmosphere

5.2: 0.58 h / -78 - 20 °C / Inert atmosphere

6.1: methanol / benzene; hexane / 0.08 h / 0 °C / Inert atmosphere

7.1: diisobutylaluminium hydride / hexane; dichloromethane / 3 h / -78 °C / Inert atmosphere

8.1: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

9.1: N,N,N',N'-tetramethylguanidine / 10 h / Inert atmosphere

10.1: sulfuric acid / 2 h / 0 °C

11.1: triethylamine / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

12.1: sodium tetrahydroborate; ethanol / 1,4-dioxane / 7 h / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; dirhodium tetraacetate; sodium tetrahydroborate; tris(triphenylphosphine)rhodium(l) chloride; ethanol; sulfuric acid; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; isopropyl alcohol; trifluoroacetic acid; lithium diisopropyl amide; N,N,N',N'-tetramethylguanidine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; benzene; 8.1: |Dess-Martin Oxidation;
DOI:10.1021/ol500657f