[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

Base Information

Chemical Name:[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol
CAS No.:1582752-99-5
Molecular Formula:C₃₀H₄₀O₃Si
Molecular Weight:476.731
Hs Code.:

Synonyms:[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

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Chemical Property of [2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

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Technology Process of [2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

There total 8 articles about [2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol 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: 85.0%

: 1582752-95-1
methyl [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carboxylate

: 1582752-99-5
[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 3h; Inert atmosphere;
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

: 1582752-99-5
[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

Guidance literature:: Multi-step reaction with 7 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

With pyridine; methanol; dirhodium tetraacetate; tris(triphenylphosphine)rhodium(l) chloride; diisobutylaluminium hydride; triphenylphosphine; isopropyl alcohol; trifluoroacetic acid; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ol500657f

Reference yield:

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

: 1582752-99-5
[2S,2(1S),5S]-[5-(tert-butyldiphenylsilyloxy)methyl-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-yl]methanol

Guidance literature:: Multi-step reaction with 8 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

With pyridine; methanol; dirhodium tetraacetate; tris(triphenylphosphine)rhodium(l) chloride; diisobutylaluminium hydride; triphenylphosphine; isopropyl alcohol; trifluoroacetic acid; lithium hexamethyldisilazane; lithium diisopropyl amide; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; dimethyl sulfoxide; benzene;
DOI:10.1021/ol500657f