(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

Base Information

Chemical Name:(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one
CAS No.:350246-29-6
Molecular Formula:C₂₉H₃₉NO₆Si
Molecular Weight:525.717
Hs Code.:

Synonyms:(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

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Chemical Property of (2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

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Technology Process of (2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

There total 15 articles about (2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-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: 91.0%

: 350246-28-5
(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-methylene-piperidine

: 350246-29-6
(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

Guidance literature:: With ozone; triphenylphosphine; In dichloromethane;
DOI:10.1016/S0040-4039(98)02618-5

Reference yield:

: 22927-31-7
4-oxobutyl benzoate

: 350246-29-6
(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

2.1: 2.25 g / toluene / 24 h / 70 °C

3.1: H₂ / 20percent Pd/C / methanol / 48 h

4.1: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

5.1: 72 percent / nBu₃P / tetrahydrofuran / 2 h

6.1: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

7.1: O₃ / CH₂Cl₂

7.2: 88 percent / PPh₃ / CH₂Cl₂ / 2 h / 20 °C

With tributylphosphine; hydrogen; sodium hydrogencarbonate; magnesium sulfate; ozone; 3-chloro-benzenecarboperoxoic acid; 20percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene;
DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2

Reference yield:

: 220861-59-6
(R)-tert-butyl 3-((tert-butyldimethylsilyl)oxy)pent-4-enoate

: 350246-29-6
(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)piperidin-3-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 79 percent / DIBAL / hexane; toluene / 0.5 h / -78 °C

2.1: 98 percent / H₂NOH*HCl / aq. ethanol / 14 h / 20 °C

3.1: sodium cyanoborohydride; HCl / methanol / 0.5 h / -10 °C

4.1: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

5.1: 2.25 g / toluene / 24 h / 70 °C

6.1: H₂ / 20percent Pd/C / methanol / 48 h

7.1: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

8.1: 72 percent / nBu₃P / tetrahydrofuran / 2 h

9.1: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

10.1: O₃ / CH₂Cl₂

10.2: 88 percent / PPh₃ / CH₂Cl₂ / 2 h / 20 °C

With hydrogenchloride; tributylphosphine; hydroxylamine hydrochloride; hydrogen; diisobutylaluminium hydride; sodium cyanoborohydride; sodium hydrogencarbonate; magnesium sulfate; ozone; 3-chloro-benzenecarboperoxoic acid; 20percent Pd/C; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; toluene;
DOI:10.1002/1521-3765(20010504)7:9<1845::AID-CHEM1845>3.0.CO;2-2