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

Base Information

Chemical Name:(2S)-(1'S,2'S)-3'-[(tert-butyldimethylsilyl)oxy]-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine
CAS No.:617700-47-7
Molecular Formula:C₂₃H₃₆N₂O₇SSi
Molecular Weight:512.7
Hs Code.:

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

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

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Technology Process of (2S)-(1'S,2'S)-3'-[(tert-butyldimethylsilyl)oxy]-[1',2'-(isopropylidenedioxy)propyl]-N-(2-nitrobenzenesulfonyl)-3,4-dehydro-piperidine

There total 13 articles about (2S)-(1'S,2'S)-3'-[(tert-butyldimethylsilyl)oxy]-[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: 92.0%

: 617700-46-6
(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)(but-3-enyl)amino]-oct-3-ene

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

Guidance literature:: Grubbs catalyst first generation; In benzene; Heating;
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

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

Guidance literature:: Multi-step reaction with 2 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

With triphenylphosphine; diethylazodicarboxylate; Grubbs catalyst first generation; In toluene; benzene;
DOI:10.1002/chem.200400830

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 7 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

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