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

Base Information

Chemical Name:(2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-methylene-piperidine
CAS No.:350246-28-5
Molecular Formula:C₃₀H₄₁NO₅Si
Molecular Weight:523.745
Hs Code.:

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

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

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

There total 16 articles about (2S,4R)-N-Benzyloxycarbonyl-2-(3-benzoyloxypropyl)-4-(tert-butyldimethylsilyloxy)-3-methylene-piperidine 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: 85.0%

: 350246-27-4
(2S,3R,4R)-2-(3-Benzoyloxy-propyl)-4-(tert-butyl-dimethyl-silanyloxy)-3-(2-nitro-phenylselanylmethyl)-piperidine-1-carboxylic acid benzyl ester

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

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane;
DOI:10.1016/S0040-4039(98)02618-5

Reference yield:

: 22927-31-7
4-oxobutyl benzoate

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

Guidance literature:: Multi-step reaction with 6 steps

1: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

2: 2.25 g / toluene / 24 h / 70 °C

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

4: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

5: 72 percent / nBu₃P / tetrahydrofuran / 2 h

6: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

With tributylphosphine; hydrogen; sodium hydrogencarbonate; magnesium sulfate; 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:

: 220861-39-2
(R)-3-((tert-butyldimethylsilyl)oxy)pent-4-enal

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

Guidance literature:: Multi-step reaction with 8 steps

1: 98 percent / H₂NOH*HCl / aq. ethanol / 14 h / 20 °C

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

3: MgSO₄ / CH₂Cl₂ / 1 h / 0 °C

4: 2.25 g / toluene / 24 h / 70 °C

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

6: 2.88 g / NaHCO₃ / diethyl ether / 20 h / 0 °C

7: 72 percent / nBu₃P / tetrahydrofuran / 2 h

8: 85 percent / mCPBA / CH₂Cl₂ / 0.08 h

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