(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

Base Information

Chemical Name:(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one
CAS No.:207738-29-2
Molecular Formula:C₃₀H₄₁NO₄Si
Molecular Weight:507.745
Hs Code.:

Synonyms:(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

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Chemical Property of (+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

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

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Technology Process of (+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

There total 15 articles about (+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-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: 70.0%

: 229160-74-1
4-((2S,3S)-1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-hydroxy-pyrrolidin-3-yl)butan-2-one

: 207738-29-2
(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

Guidance literature:: With quinolinium camphor-10-sulfonate; In toluene; at 80 ℃; for 0.333333h;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 207738-29-2
(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

Guidance literature:: Multi-step reaction with 10 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

8.1: 90 percent / DiBAl-H / tetrahydrofuran; hexane / 2 h / -78 °C

9.1: 50 percent / HCl / acetone; H₂O / 6 h / 20 °C

10.1: 70 percent / quinolinium camphorsulfonate / toluene / 0.33 h / 80 °C

With 1H-imidazole; hydrogenchloride; dmap; quinolinium camphor-10-sulfonate; dihydrogen peroxide; sodium naphthalenide; diisobutylaluminium hydride; magnesium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; 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 / 8.1: Reduction / 9.1: Hydrolysis / 10.1: Dehydration;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

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

: 207738-29-2
(+)-4-(2S,3S)-(1-(tert-butoxycarbonyl)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-2,3-dihydro-1H-pyrrol-3-yl)butan-2-one

Guidance literature:: Multi-step reaction with 9 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

7.1: 90 percent / DiBAl-H / tetrahydrofuran; hexane / 2 h / -78 °C

8.1: 50 percent / HCl / acetone; H₂O / 6 h / 20 °C

9.1: 70 percent / quinolinium camphorsulfonate / toluene / 0.33 h / 80 °C

With hydrogenchloride; dmap; quinolinium camphor-10-sulfonate; dihydrogen peroxide; sodium naphthalenide; diisobutylaluminium hydride; magnesium; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; water; ethyl acetate; acetone; toluene; 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 / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Dehydration;
DOI:10.1016/S0040-4020(99)00284-7