(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

Base Information

Chemical Name:(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol
CAS No.:229160-62-7
Molecular Formula:C₃₂H₃₉NO₄SSi
Molecular Weight:561.817
Hs Code.:

Synonyms:(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

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Chemical Property of (2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

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Technology Process of (2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

There total 10 articles about (2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol 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: 72.0%

: 229160-61-6
(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-1-tosyl-4-[4-(trimethylsilyl)but-3-ynyl]pyrrolidin-2-ol

: 229160-62-7
(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

Guidance literature:: With potassium carbonate; In methanol; at 20 ℃; for 15h;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

: 17342-08-4
(S)-Pyroglutaminol

: 229160-62-7
(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

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: 56 percent / trimethylsilyl chloride / tetrahydrofuran / 0.25 h / -78 °C

6.1: 85 percent / DiBAl-H / CH₂Cl₂; hexane / 1 h / -78 °C

7.1: 72 percent / K₂CO₃ / methanol / 15 h / 20 °C

With 1H-imidazole; dihydrogen peroxide; diisobutylaluminium hydride; potassium carbonate; magnesium; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; 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: Reduction / 7.1: Hydrolysis;
DOI:10.1016/S0040-4020(99)00284-7

Reference yield:

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

: 229160-62-7
(2SR,4S,5S)-5-{[(tert-butyldiphenylsilyl)oxy]methyl}-4-but-3-ynyl-1-tosylpyrrolidin-2-ol

Guidance literature:: Multi-step reaction with 3 steps

1.1: magnesium / tetrahydrofuran

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

1.3: 56 percent / trimethylsilyl chloride / tetrahydrofuran / 0.25 h / -78 °C

2.1: 85 percent / DiBAl-H / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 72 percent / K₂CO₃ / methanol / 15 h / 20 °C

With diisobutylaluminium hydride; potassium carbonate; magnesium; In tetrahydrofuran; methanol; hexane; dichloromethane; 1.1: Alkylation / 1.2: Alkylation / 1.3: Alkylation / 2.1: Reduction / 3.1: Hydrolysis;
DOI:10.1016/S0040-4020(99)00284-7