(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

Base Information

Chemical Name:(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate
CAS No.:105087-22-7
Molecular Formula:C₂₉H₄₀O₅Si
Molecular Weight:496.719
Hs Code.:

Synonyms:(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

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Chemical Property of (2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

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Technology Process of (2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

There total 10 articles about (2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-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: 96.0%

: 104705-89-7
(2R,4R,6S,8R,9S)-methyl 4-hydroxy-8,9-dimethyl-1,7-dioxaspiro-<5,5>undecane-2-carboxylate

: 58479-61-1
tert-butylchlorodiphenylsilane

: 105087-22-7
(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 1h;
DOI:10.1021/jo00375a017

Reference yield:

: 82467-25-2
(+)-(5S,6R)-tetrahydro-5,6-dimethyl-2H-pyran-2-one

: 105087-22-7
(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

2: TsOH*H₂O / CH₂Cl₂ / 0.5 h

3: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

4: 96 percent / imidazole / dimethylformamide / 1 h / 0 - 20 °C

With 1H-imidazole; hydrogen; toluene-4-sulfonic acid; lithium diisopropyl amide; rhodium on aluminium; In ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00375a017

Reference yield:

: 2436-90-0
(S)-(+)-dihydromyrcene

: 105087-22-7
(2R,4R,6S,8R,9S)-methyl 4<(tert-butyldiphenylsilyl)oxy>-8,9-dimethyl-1,7-dioxaspiro<5.5>undecane-2-carboxylate

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) ozone, 2.) Me₂S / 1.) CH₂Cl₂, -78 degC, 1.5 h, 2.) CH₂Cl₂, from -78 deg C to RT

2: CrO₃, aq. H₂SO₄ / acetone / 0 - 10 °C

3: 85 percent / I₂ / acetonitrile / 1.) -25 deg C, 10 h, 2.) 0 deg C, 4 h

4: 90 percent / Bu₃SnH / benzene / 2 h / Heating

5: 1.) LDA / 1.) THF, a) -78 deg C, 10 min, b) 0 deg C, 1 h, 2.) THF, a) -78 deg C, 15 min, b) 0 deg C, 1 h

6: TsOH*H₂O / CH₂Cl₂ / 0.5 h

7: 58 percent / H₂ / 5percent Rh/Al / ethanol / 2 h

8: 96 percent / imidazole / dimethylformamide / 1 h / 0 - 20 °C

With 1H-imidazole; chromium(VI) oxide; dimethylsulfide; sulfuric acid; hydrogen; iodine; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; ozone; lithium diisopropyl amide; rhodium on aluminium; In ethanol; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; benzene;
DOI:10.1021/jo00375a017