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

Base Information

Chemical Name:methyl [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carboxylate
CAS No.:1582752-95-1
Molecular Formula:C₃₁H₄₀O₄Si
Molecular Weight:504.742
Hs Code.:

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

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

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

There total 7 articles about methyl [2S,2(1S),5S]-5-[(tert-butyldiphenylsilyl)oxymethyl]-2-(1-methylcyclohex-2-en-1-yl)-3-methylenetetrahydrofuran-2-carboxylate 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:

: 1582752-93-9
C₃₀H₃₈O₄Si

: 18107-18-1
diazomethyl-trimethyl-silane

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

Guidance literature:: With methanol; In hexane; benzene; at 0 ℃; for 0.0833333h; Inert atmosphere;
DOI:10.1021/ol500657f

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; methanol; dirhodium tetraacetate; tris(triphenylphosphine)rhodium(l) chloride; 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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With pyridine; methanol; dirhodium tetraacetate; tris(triphenylphosphine)rhodium(l) chloride; 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