(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

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Chemical Name:(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one
CAS No.:193264-87-8
Molecular Formula:C₃₂H₄₅NO₆Si
Molecular Weight:567.798
Hs Code.:

Synonyms:(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

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Chemical Property of (-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

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Technology Process of (-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

There total 10 articles about (-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-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: 95.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 229160-72-9
(+)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

: 193264-87-8
(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 20 ℃; for 24h;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 193264-87-8
(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / imidazole / dimethylformamide / 24 h / 20 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -20 °C

2.2: 98 percent / tetrahydrofuran; hexane / -20 - 20 °C

3.1: LiHMDS / tetrahydrofuran; hexane / 2 h

3.2: 85 percent / tetrahydrofuran; hexane / -78 - 20 °C

4.1: 75 percent / hydrogen peroxide / ethyl acetate / 0 - 20 °C

5.1: magnesium / tetrahydrofuran

5.2: CuBr*Me₂S / tetrahydrofuran / 0.17 h / -78 °C

5.3: 71 percent / trimethylsilyl chloride / tetrahydrofuran / 0.17 h / -78 °C

6.1: 90 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.17 h

7.1: 95 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With 1H-imidazole; dmap; dihydrogen peroxide; sodium naphthalenide; magnesium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Tosylation / 2.2: Tosylation / 3.1: Metallation / 3.2: phenylselenylation / 4.1: Oxidation / 5.1: Alkylation / 5.2: Alkylation / 5.3: Alkylation / 6.1: desulfonation / 7.1: tert-butoxycarbonylation;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 132974-83-5
(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one

: 193264-87-8
(-)-(4S,5S)-1-(tert-butoxycarbonyl)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 1 h / -20 °C

1.2: 98 percent / tetrahydrofuran; hexane / -20 - 20 °C

2.1: LiHMDS / tetrahydrofuran; hexane / 2 h

2.2: 85 percent / tetrahydrofuran; hexane / -78 - 20 °C

3.1: 75 percent / hydrogen peroxide / ethyl acetate / 0 - 20 °C

4.1: magnesium / tetrahydrofuran

4.2: CuBr*Me₂S / tetrahydrofuran / 0.17 h / -78 °C

4.3: 71 percent / trimethylsilyl chloride / tetrahydrofuran / 0.17 h / -78 °C

5.1: 90 percent / sodium naphthalenide / 1,2-dimethoxy-ethane / 0.17 h

6.1: 95 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 24 h / 20 °C

With dmap; dihydrogen peroxide; sodium naphthalenide; magnesium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; ethyl acetate; 1.1: Tosylation / 1.2: Tosylation / 2.1: Metallation / 2.2: phenylselenylation / 3.1: Oxidation / 4.1: Alkylation / 4.2: Alkylation / 4.3: Alkylation / 5.1: desulfonation / 6.1: tert-butoxycarbonylation;
DOI:10.1016/S0040-4020(99)00284-7