(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Base Information

Chemical Name:(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone
CAS No.:185903-71-3
Molecular Formula:C₂₀H₃₈O₄Si
Molecular Weight:370.605
Hs Code.:

Synonyms:(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

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Chemical Property of (2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

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Technology Process of (2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

There total 7 articles about (2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone 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: 97.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 185903-68-8
(2R,5S,6R)-2-Hydroxymethyl-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

: 185903-71-3
(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; Ambient temperature;
DOI:10.1016/S0040-4039(96)02191-0

Reference yield:

: 3973-43-1
4-methylpent-4-enal

: 185903-71-3
(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1: 99 percent / nBu₂BOTf, iPr₂NEt / CH₂Cl₂ / -78 °C

2: PPTS / CH₂Cl₂ / Heating

3: LiAlH₄ / tetrahydrofuran

4: Swern ox.

5: NH₂OH*HCl, AcONa / methanol / Ambient temperature

6: 88 percent / 7percent aq. NaOCl / CH₂Cl₂ / 8 h / Ambient temperature

7: 88 percent / H₂, B(OMe)3 / Raney Ni / H₂O; methanol / 1471.02 Torr / Ambient temperature

8: 97 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; sodium hypochlorite; lithium aluminium tetrahydride; Trimethyl borate; di-n-butylboryl trifluoromethanesulfonate; hydroxylamine hydrochloride; hydrogen; sodium acetate; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; nickel; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(96)02191-0

Reference yield:

: (2R,3S)-2,6-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-hept-6-enal

: 185903-71-3
(2R,5S,6R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-2,6-dimethyl-5-(tetrahydro-pyran-2-yloxy)-cyclohexanone

Guidance literature:: Multi-step reaction with 4 steps

1: NH₂OH*HCl, AcONa / methanol / Ambient temperature

2: 88 percent / 7percent aq. NaOCl / CH₂Cl₂ / 8 h / Ambient temperature

3: 88 percent / H₂, B(OMe)3 / Raney Ni / H₂O; methanol / 1471.02 Torr / Ambient temperature

4: 97 percent / imidazole / dimethylformamide / Ambient temperature

With 1H-imidazole; sodium hypochlorite; Trimethyl borate; hydroxylamine hydrochloride; hydrogen; sodium acetate; nickel; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4039(96)02191-0