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

Base Information

Chemical Name:(-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1-tosylpyrrolidin-2-one
CAS No.:207738-28-1
Molecular Formula:C₃₄H₄₃NO₆SSi
Molecular Weight:621.87
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 11 articles about (-)-(4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-[2-(2-methyl-1,3-dioxolan-2-yl)ethyl]-1-tosylpyrrolidin-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: 71.0%

: 2-(2-methyl-1,3-dioxolan-2-yl)ethylmagnesium bromide

: 132974-85-7
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one

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

Guidance literature:: With copper(I) bromide; In tetrahydrofuran; at -78 ℃;
DOI:10.1055/s-1998-1694

Reference yield: 71.0%

: 37865-96-6
2-(2-bromoethyl)-2-methyl-1,3-dioxolane

: 132974-85-7
(-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one

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

Guidance literature:: With magnesium; In tetrahydrofuran;

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -78 ℃; for 0.166667h;

2-(2-bromoethyl)-2-methyl-1,3-dioxolane; (-)-(5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-1,5-dihydro-2H-pyrrol-2-one; With chloro-trimethyl-silane; In tetrahydrofuran; at -78 ℃; for 0.166667h;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

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

Guidance literature:: Multi-step reaction with 5 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

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