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

Base Information

• Chemical Name: (2S)-{(1'S,2'S)-1',2'-(isopropylidenedioxy)-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine
• CAS No.: 617700-49-9
• Molecular Formula: C₂₄H₂₈N₂O₉S₂
• Molecular Weight: 552.626
• Mol file: 617700-49-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 15 articles about (2S)-{(1'S,2'S)-1',2'-(isopropylidenedioxy)-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine 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: 91.0%

p-toluenesulfonyl chloride (98-59-9) + (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-48-8) → (2S)-{(1'S,2'S)-1',2'-(isopropylidenedioxy)-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-49-9)

Guidance literature:

DOI:10.1055/s-2003-39314

Reference yield:

(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)amino]-oct-3-ene (617700-45-5) → (2S)-{(1'S,2'S)-1',2'-(isopropylidenedioxy)-3'-[(p-toluenesulfonyl)oxy]propyl}-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-49-9)

Guidance literature:

Multi-step reaction with 4 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

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

Guidance literature:

Multi-step reaction with 9 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

With 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

upstream raw materials:

p-toluenesulfonyl chloride

(2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine

Carbamic acid (E)-(S)-3-[(4S,5S)-5-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-1-ethyl-allyl ester

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

Downstream raw materials:

(+)-lentiginosine

Toluene-4-sulfonic acid (2S,3S)-2,3-bis-methoxymethoxy-3-[(S)-1-(2-nitro-benzenesulfonyl)-1,2,5,6-tetrahydro-pyridin-2-yl]-propyl ester

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