tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

Base Information

Chemical Name:tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate
CAS No.:773889-93-3
Molecular Formula:C₁₆H₂₆O₃
Molecular Weight:266.381
Hs Code.:

Synonyms:tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

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Chemical Property of tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

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Technology Process of tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

There total 1 articles about tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]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:

: 540-88-5
acetic acid tert-butyl ester

: 6485-40-1,2244-16-8
(R)-Carvone

: tert-butyl 2-[(1R,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

: 773889-93-3
tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

Guidance literature:: acetic acid tert-butyl ester; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -78 ℃; for 0.416667h;

(R)-Carvone; In tetrahydrofuran; hexane; at -78 ℃; for 2h; Title compound not separated from byproducts;
DOI:10.1007/s00706-003-0153-7

Reference yield: 84.0%

: 773889-93-3
tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

: 773889-84-2
(1S,5R)-1-(2-hydroxyethyl)-2-methyl-5-(prop-1-en-2-yl)cyclohex-2-enol

Guidance literature:: With lithium aluminium tetrahydride; In diethyl ether; at 20 ℃; for 2h;
DOI:10.1007/s00706-003-0153-7

Reference yield:

: 773889-93-3
tert-butyl 2-[(1S,5R)-1-hydroxy-5-isopropenyl-2-methyl-2-cyclohexenyl]acetate

: 773889-90-0
(6R,7S,8S,10S)-10-benzyloxy-7,8-epoxy-2,2,7-trimethyl-1,3-dioxaspiro[5.5]undecane

Guidance literature:: Multi-step reaction with 7 steps

1.1: 84 percent / LiAlH₄ / diethyl ether / 2 h / 20 °C

2.1: MCPBA / CH₂Cl₂ / -40 - -10 °C

3.1: 80 percent / PPTS / CH₂Cl₂ / 0.5 h / 0 °C

4.1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

4.2: Ac₂O; Et₃N; DMPA / CH₂Cl₂; methanol / 12 h / Heating

4.3: 74 percent / K₂CO₃ / methanol / 2 h / 20 °C

5.1: 94 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 24 h / 0 °C

6.1: 93 percent / NaOH / methanol / 5 h / 20 °C

7.1: NaH / dimethylformamide / 0.08 h / 0 °C

7.2: 90 percent / dimethylformamide; tetrahydrofuran / 2 h / 20 °C

With sodium hydroxide; lithium aluminium tetrahydride; di-isopropyl azodicarboxylate; pyridinium p-toluenesulfonate; sodium hydride; sodium hydrogencarbonate; ozone; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 4.2: Criegee rearrangement / 5.1: Mitsunobu reaction;
DOI:10.1007/s00706-003-0153-7