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

Base Information

Chemical Name:(3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)(but-3-enyl)amino]-oct-3-ene
CAS No.:617700-46-6
Molecular Formula:C₂₇H₄₄N₂O₇SSi
Molecular Weight:568.807
Hs Code.:

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

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

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

There total 13 articles about (3E,5S,6S,7S)-8-[(tert-butyldimethylsilyl)oxy]-6,7-(isopropylidenedioxy)-5-[(2-nitrobenzenesulfonyl)(but-3-enyl)amino]-oct-3-ene 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: 89.0%

: 627-27-0
homoalylic alcohol

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

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

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In toluene; benzene; at 20 ℃; for 7h;
DOI:10.1002/chem.200400830

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

With carbon tetrabromide; sodium hydrogencarbonate; acetic acid; triethylamine; triphenylphosphine; zinc; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; toluene; 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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

With sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; In dichloromethane; toluene; benzene;
DOI:10.1002/chem.200400830