(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

Base Information

Chemical Name:(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one
CAS No.:332097-64-0
Molecular Formula:C₁₇H₃₂O₄Si
Molecular Weight:328.524
Hs Code.:

Synonyms:(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

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Chemical Property of (3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

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Technology Process of (3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

There total 6 articles about (3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one 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: 100.0%

: 332097-63-9
(1R,3R,5R)-1-hydroxy-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexane

: 332097-64-0
(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; potassium bromide; sodium hydrogencarbonate; In dichloromethane; water; at 0 ℃; for 1h;
DOI:10.1016/S0040-4020(00)01035-8

Reference yield:

: 50409-12-6,13314-30-2
cis,cis-1,3,5-trihydroxycyclohexane

: 332097-64-0
(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N; NaH / tetrahydrofuran / 2.5 h / 22 - 45 °C

2: 99 percent / Lipase QL / ethyl acetate / 46 h / 22 °C

3: 93 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 °C

4: 98 percent / K₂CO₃ / methanol; H₂O / 7 h / 22 °C

5: 100 percent / NaOCl; TEMPO; KBr / NaHCO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; Lipase QL; di-isopropyl azodicarboxylate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 3: Mitsunobu reaction;
DOI:10.1016/S0040-4020(00)01035-8

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 332097-64-0
(3S,5S)-3-tert-butylcarbonyloxy-5-(tert-butyldimethylsilanyloxy)-cyclohexan-1-one

Guidance literature:: Multi-step reaction with 5 steps

1: 93 percent / Et₃N; NaH / tetrahydrofuran / 2.5 h / 22 - 45 °C

2: 99 percent / Lipase QL / ethyl acetate / 46 h / 22 °C

3: 93 percent / PPh₃; diisopropyl azodicarboxylate / tetrahydrofuran / 2 h / 0 °C

4: 98 percent / K₂CO₃ / methanol; H₂O / 7 h / 22 °C

5: 100 percent / NaOCl; TEMPO; KBr / NaHCO₃ / CH₂Cl₂; H₂O / 1 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; Lipase QL; di-isopropyl azodicarboxylate; sodium hydride; potassium carbonate; triethylamine; triphenylphosphine; potassium bromide; sodium hydrogencarbonate; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; 3: Mitsunobu reaction;
DOI:10.1016/S0040-4020(00)01035-8