(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

Base Information

Chemical Name:(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate
CAS No.:278801-11-9
Molecular Formula:C₁₇H₂₈O₃Si
Molecular Weight:308.493
Hs Code.:

Synonyms:(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

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Chemical Property of (+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

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Technology Process of (+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

There total 6 articles about (+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate 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: 38.0%

: 108-24-7
acetic anhydride

: 278799-78-3
(+)-(1S,5S)-3-ethynyl-5-isopropenyl-2-methylcyclohex-2-enyl tert-butyldimethylsilyl ether

: 278801-11-9
(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

Guidance literature:: (+)-(1S,5S)-3-ethynyl-5-isopropenyl-2-methylcyclohex-2-enyl tert-butyldimethylsilyl ether; With oxygen; sodium hydrogencarbonate; ozone; In methanol; dichloromethane; at -70 ℃;

acetic anhydride; With dmap; triethylamine; In benzene; at 20 ℃; for 7h; Heating;
DOI:10.1016/S0040-4039(00)00325-7

Reference yield:

: 278799-73-8
(+)-(1S,5S)-3-ethynyl-5-isopropenyl-2-methylcyclohex-2-enol

: 278801-11-9
(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

Guidance literature:: Multi-step reaction with 2 steps

1.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 4 h / 20 °C

2.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / 0.03 h / cooling

2.2: 34 percent / triethylamine; DMAP / benzene / Heating

With 1H-imidazole; dmap; sodium hydrogencarbonate; ozone; In methanol; dichloromethane;

Reference yield:

: 278799-72-7
(+)-(5S)-3-ethynyl-5-isopropenyl-2-methylcyclohex-2-enone

: 278801-11-9
(+)-(1S,5S)-5-(tert-butyldimethylsilyloxy)-3-ethynyl-4-methylcyclohex-3-enyl acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 98 percent / lithium aluminium hydride / diethyl ether / 2 h / -70 °C

2.1: 97 percent / imidazole; DMAP / CH₂Cl₂ / 4 h / 20 °C

3.1: ozone; NaHCO₃ / CH₂Cl₂; methanol / 0.03 h / cooling

3.2: 34 percent / triethylamine; DMAP / benzene / Heating

With 1H-imidazole; dmap; lithium aluminium tetrahydride; sodium hydrogencarbonate; ozone; In methanol; diethyl ether; dichloromethane;