(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

Base Information

Chemical Name:(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone
CAS No.:1377419-06-1
Molecular Formula:C₂₄H₄₄O₄Si
Molecular Weight:424.696
Hs Code.:

Synonyms:(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

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Chemical Property of (2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

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Technology Process of (2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

There total 12 articles about (2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone 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: 68.0%

: 1377418-94-4
2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-2-methylcyclohexane-1,3-dione

: 1377419-06-1
(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

: 1377418-95-5
(2R,3R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

Guidance literature:: With sodium tetrahydroborate; cerium(III) chloride heptahydrate; In tetrahydrofuran; methanol; at -78 ℃; for 0.333333h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;
DOI:10.1002/anie.201200515

Reference yield:

: tert-butyl(((1R,5R)-5-isopropyl-2-methylcyclohex-2-en-1-yl)oxy)dimethylsilane

: 1377419-06-1
(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

: 1377418-95-5
(2R,3R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

Guidance literature:: Multi-step reaction with 9 steps

1.1: ozone / methanol; dichloromethane / -78 °C

1.2: 1.25 h / -78 - 20 °C

2.1: piperidine; acetic acid / diethyl ether / 20 h / 70 °C / Inert atmosphere

3.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

4.1: mercury(II) diacetate / 24 h / 60 °C / Inert atmosphere

5.1: toluene / 16 h / 173 °C / Inert atmosphere

6.1: L-proline / dichloromethane / 3 h / 20 °C / Inert atmosphere

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

7.2: 14 h / 80 °C / Inert atmosphere

8.1: ozone / dichloromethane / -78 °C

8.2: 0.5 h / -78 - 20 °C

9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere

With piperidine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 5.1: Claisen rearrangement / 6.1: Knoevenagel condensation / 7.1: Heck reaction / 7.2: Heck reaction / 9.1: Luche reduction;
DOI:10.1002/anie.201200515

Reference yield:

: (3S,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-6-oxoheptanal

: 1377419-06-1
(2S,3S)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

: 1377418-95-5
(2R,3R)-2-(2-((1S,3R,5R)-5-((tert-butyldimethylsilyl)oxy)-3-isopropyl-1-methyl-2-oxocyclopentyl)ethyl)-3-hydroxy-2-methylcyclohexanone

Guidance literature:: Multi-step reaction with 8 steps

1.1: piperidine; acetic acid / diethyl ether / 20 h / 70 °C / Inert atmosphere

2.1: sodium tetrahydroborate / methanol / 0.25 h / 0 °C

3.1: mercury(II) diacetate / 24 h / 60 °C / Inert atmosphere

4.1: toluene / 16 h / 173 °C / Inert atmosphere

5.1: L-proline / dichloromethane / 3 h / 20 °C / Inert atmosphere

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium iodide / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

6.2: 14 h / 80 °C / Inert atmosphere

7.1: ozone / dichloromethane / -78 °C

7.2: 0.5 h / -78 - 20 °C

8.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / tetrahydrofuran; methanol / 0.33 h / -78 °C / Inert atmosphere

With piperidine; sodium tetrahydroborate; cerium(III) chloride heptahydrate; mercury(II) diacetate; ozone; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; L-proline; lithium iodide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 4.1: Claisen rearrangement / 5.1: Knoevenagel condensation / 6.1: Heck reaction / 6.2: Heck reaction / 8.1: Luche reduction;
DOI:10.1002/anie.201200515