methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

Base Information

Chemical Name:methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate
CAS No.:1374759-96-2
Molecular Formula:C₂₄H₃₉NO₅SSi
Molecular Weight:481.729
Hs Code.:

Synonyms:methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

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Chemical Property of methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

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Technology Process of methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

There total 6 articles about methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate 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%

: Tebbe's reagent

: 1374759-91-7
methyl-2-((2S,3S,4R)-4-acetyl-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylpyrrolidin-3-yl)acetate

: 1374759-96-2
methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:: methyl-2-((2S,3S,4R)-4-acetyl-2-(((tert-butyldimethylsilyl)oxy)methyl)-1-tosylpyrrolidin-3-yl)acetate; With pyridine; In tetrahydrofuran; at -40 ℃; for 0.166667h;

Tebbe's reagent; In tetrahydrofuran; at -40 - 20 ℃; for 20h;
DOI:10.1021/ol3008414

Reference yield:

: N-((1S)-1-(2-benzoylcyclopropyl)-2-((tert-butyldimethylsilyl)oxy)ethyl)-N-(but-2-yn-1-yl)-4-methylbenzenesulfonamide

: 1374759-96-2
methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:: Multi-step reaction with 6 steps

1.1: samarium diiodide / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 20 °C

3.1: ozone / methanol; dichloromethane / 0.75 h / -78 °C

3.2: 20 °C

4.1: dihydrogen peroxide; sodium hydroxide / 1,4-dioxane; water / 0.17 h / 0 °C

5.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

6.1: pyridine / tetrahydrofuran / 0.17 h / -40 °C

6.2: 20 h / -40 - 20 °C

With pyridine; samarium diiodide; dihydrogen peroxide; potassium carbonate; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol3008414

Reference yield:

: C₂₉H₃₉NO₆SSi

: 1374759-96-2
methyl-2-((2S,3S,4S)-2-(((tert-butyldimethylsilyl)oxy)methyl)-4-(prop-1-en-2-yl)-1-tosylpyrrolidin-3-yl)acetate

Guidance literature:: Multi-step reaction with 3 steps

1.1: dihydrogen peroxide; sodium hydroxide / 1,4-dioxane; water / 0.17 h / 0 °C

2.1: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

3.1: pyridine / tetrahydrofuran / 0.17 h / -40 °C

3.2: 20 h / -40 - 20 °C

With pyridine; dihydrogen peroxide; potassium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol3008414