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

Base Information

• Chemical Name: (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine
• CAS No.: 617700-48-8
• Molecular Formula: C₁₇H₂₂N₂O₇S
• Molecular Weight: 398.437
• Mol file: 617700-48-8.mol

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

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

There total 14 articles about (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)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%

(2S)-(1'S,2'S)-3'-[(tert-butyldimethylsilyl)oxy]-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-47-7) → (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-48-8)

Guidance literature:

With tetrabutyl ammonium fluoride;

DOI:10.1055/s-2003-39314

Reference yield:

(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)(but-3-enyl)amino]-oct-3-ene (617700-46-6) → (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / Cl₂Ru(PCy₃)2=CHPh / benzene / 1.5 h / 60 °C

2: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran; acetonitrile / 6 h / 20 °C

With tetrabutyl ammonium fluoride; Grubbs catalyst first generation; In tetrahydrofuran; acetonitrile; benzene;

DOI:10.1002/chem.200400830

Reference yield:

(E)-1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-pent-2-enylamine → (2S)-(1'S,2'S)-3'-hydroxy-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine (617700-48-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 285 mg / aq. NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

2: 89 percent / diethyl azodicarboxylate; PPh₃ / benzene; toluene / 7 h / 20 °C

3: 92 percent / Cl₂Ru(PCy₃)2=CHPh / benzene / 1.5 h / 60 °C

4: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran; acetonitrile / 6 h / 20 °C

With tetrabutyl ammonium fluoride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; Grubbs catalyst first generation; In tetrahydrofuran; dichloromethane; toluene; acetonitrile; benzene;

DOI:10.1002/chem.200400830

upstream raw materials:

(2S)-(1'S,2'S)-3'-[(tert-butyldimethylsilyl)oxy]-[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

2-Nitrobenzenesulfonyl chloride

Downstream raw materials:

(+)-lentiginosine

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

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