(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

Base Information

Chemical Name:(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine
CAS No.:1500059-31-3
Molecular Formula:C₃₀H₃₅NO₃SSi
Molecular Weight:517.764
Hs Code.:

Synonyms:(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

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Chemical Property of (2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

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Technology Process of (2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

There total 8 articles about (2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine 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:

: 17342-08-4
(S)-Pyroglutaminol

: 1500059-31-3
(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

: 1500059-33-5
C₃₀H₃₅NO₃SSi

Guidance literature:: Multi-step reaction with 6 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 68 h / 20 °C / Inert atmosphere

2.1: 1,1,1,3,3,3-hexamethyl-disilazane; n-butyllithium / tetrahydrofuran; hexane / 1 h / -20 °C / Inert atmosphere

2.2: 17 h / -20 - 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / toluene; dichloromethane / 15 h / -78 - 20 °C / Inert atmosphere

4.1: diisobutylaluminium hydride / tetrahydrofuran / 40 h / -78 - 20 °C / Inert atmosphere

5.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: sodium hydride / N,N-dimethyl-formamide / 2 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; n-butyllithium; sodium hydride; diisobutylaluminium hydride; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201300687

Reference yield:

: (6S)-7-[(tert-butyldiphenylsilyl)oxy]-6-(4-methylphenylsulfonamido)hept-1-yn-3-ylmethanesulfonate

: 1500059-31-3
(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

: 1500059-33-5
C₃₀H₃₅NO₃SSi

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2h; Overall yield = 45 %; Overall yield = 7.7 mg; Inert atmosphere;
DOI:10.1002/chem.201300687

Reference yield:

: N-{(2S)-7-bromo-1-[(tert-butyldiphenylsilyl)oxy]hepta-5,6-dien-2-yl}-4-methylbenzenesulfonamide

: 1500059-31-3
(2S,5R)-2-{[(tert-butyldiphenylsilyl)oxy]methyl}-5-ethynyl-1-tosylpyrrolidine

: 1500059-33-5
C₃₀H₃₅NO₃SSi

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 3.5h; Overall yield = 71 %; Overall yield = 28.5 mg; stereoselective reaction; Inert atmosphere;
DOI:10.1002/chem.201300687