(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

Base Information

Chemical Name:(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine
CAS No.:617700-50-2
Molecular Formula:C₂₁H₂₄N₂O₉S₂
Molecular Weight:512.562
Hs Code.:

Synonyms:(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

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Chemical Property of (2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

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Technology Process of (2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

There total 17 articles about (2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine 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: 92.0%

: 617700-49-9
(2S)-{(1'S,2'S)-1',2'-(isopropylidenedioxy)-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine

: 617700-50-2
(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

Guidance literature:: With hydrogenchloride; In tetrahydrofuran; at 50 ℃; for 6h;
DOI:10.1055/s-2003-39314

Reference yield:

: 617700-45-5
(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)amino]-oct-3-ene

: 617700-50-2
(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

Guidance literature:: Multi-step reaction with 5 steps

1: 89 percent / diethyl azodicarboxylate; PPh₃ / benzene; toluene / 7 h / 20 °C

2: 92 percent / Cl₂Ru(PCy₃)2=CHPh / benzene / 1.5 h / 60 °C

3: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran; acetonitrile / 6 h / 20 °C

4: 91 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

5: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 50 °C

With hydrogenchloride; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1002/chem.200400830

Reference yield:

: (4E,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-oct-4-en-3-ol

: 617700-50-2
(2S)-{(1'S,2'S)-1',2'-dihydroxy-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydropiperidine

Guidance literature:: Multi-step reaction with 10 steps

1.1: CH₂Cl₂ / 0.33 h / 0 °C

1.2: 95 percent / aq. K₂CO₃ / methanol / 7 h / 20 °C

2.1: CBr₄; PPh₃; Et₃N / CH₂Cl₂ / 0.33 h / -20 - 0 °C

3.1: 106 mg / CH₂Cl₂ / 3 h / 0 - 20 °C

4.1: Zn; AcOH / tetrahydrofuran / 4 h / 20 °C

5.1: 285 mg / aq. NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

6.1: 89 percent / diethyl azodicarboxylate; PPh₃ / benzene; toluene / 7 h / 20 °C

7.1: 92 percent / Cl₂Ru(PCy₃)2=CHPh / benzene / 1.5 h / 60 °C

8.1: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran; acetonitrile / 6 h / 20 °C

9.1: 91 percent / Et₃N / CH₂Cl₂ / 4 h / 20 °C

10.1: 92 percent / aq. HCl / tetrahydrofuran / 5 h / 50 °C

With hydrogenchloride; carbon tetrabromide; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;
DOI:10.1002/chem.200400830