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

Base Information

Chemical Name:(+)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]pyrrolidin-2-one
CAS No.:229160-72-9
Molecular Formula:C₂₇H₃₇NO₄Si
Molecular Weight:467.681
Hs Code.:

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

There total 9 articles about (+)-(4S,5S)-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: 90.0%

: 207738-28-1
(-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1-tosylpyrrolidin-2-one

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

Guidance literature:: With sodium naphthalenide; In 1,2-dimethoxyethane; for 0.166667h;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 229160-72-9
(+)-(4S,5S)-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: 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

With 1H-imidazole; dihydrogen peroxide; sodium naphthalenide; magnesium; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 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;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

With dihydrogen peroxide; sodium naphthalenide; magnesium; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 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;
DOI:10.1016/S0040-4020(99)00284-7