1.1: pyridine; dihydrogen peroxide / dichloromethane / 0.5 h / 20 °C 2.1: triphenylphosphine / toluene / 3 h / Reflux 3.1: 4-(N,N-dimethlyamino)pyridine; triethylamine / dichloromethane / 0 - 20 °C 4.1: boron trifluoride diethyl etherate / 3 h / -20 °C / Inert atmosphere 5.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C 5.2: 4 °C View Scheme

<b>Multi-step reaction with 8 steps<br /> </b>1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux<br />2.1: potassium carbonate / 5 h / 20 &deg;C<br />3.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 &deg;C / Inert atmosphere<br />4.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 &deg;C<br />5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 &deg;C<br />6.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 &deg;C / Inert atmosphere<br />6.2: 1 h<br />7.1: triethylamine / dichloromethane / 0.5 h / 0 &deg;C / Inert atmosphere<br />8.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 &deg;C / Inert atmosphere<br />8.2: 0.5 h / -78 &deg;C / Inert atmosphere<br />8.3: 0.5 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 &deg;C<br />2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 &deg;C<br />3.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 &deg;C / Inert atmosphere<br />3.2: 1 h<br />4.1: triethylamine / dichloromethane / 0.5 h / 0 &deg;C / Inert atmosphere<br />5.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 &deg;C / Inert atmosphere<br />5.2: 0.5 h / -78 &deg;C / Inert atmosphere<br />5.3: 0.5 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 &deg;C / Inert atmosphere<br />1.2: 1 h<br />2.1: triethylamine / dichloromethane / 0.5 h / 0 &deg;C / Inert atmosphere<br />3.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 &deg;C / Inert atmosphere<br />3.2: 0.5 h / -78 &deg;C / Inert atmosphere<br />3.3: 0.5 h<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '21222813', constants.ctx, '0')">(1S,3S,4R,5R)-ethyl 4-azido-3-(tert-butoxycarbonylamino)-5-(trimethylsilyloxy)cyclohexanecarboxylate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '906717', constants.ctx, '0')">lithium diisopropyl amide</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;0.75&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '2039772', constants.ctx, '0')">benzene-selenenyl bromide</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a> <br />T=-78&deg;C;&nbsp;0.5&nbsp;h;&nbsp;&nbsp;Inert atmosphere;&nbsp;<br />Stage #3: <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1098214', constants.ctx, '0')">hydrogenchloride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1696894', constants.ctx, '0')">diethyl ether</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '1730733', constants.ctx, '0')">hexane</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3587155', constants.ctx, '0')">water</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '969132', constants.ctx, '0')">pentane</a> <br />0.5&nbsp;h;&nbsp;<br /> <br /> &nbsp;

<b>Multi-step reaction with 9 steps<br /> </b>1.1: sodium hydrogencarbonate / water<br />1.2: 20 &deg;C / Darkness<br />2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Reflux<br />3.1: potassium carbonate / 5 h / 20 &deg;C<br />4.1: triphenylphosphine; diethylazodicarboxylate / toluene / 6 h / -20 &deg;C / Inert atmosphere<br />5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; 2-hydroxyethanethiol / acetone / 3 h / 20 &deg;C<br />6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / 0 &deg;C<br />7.1: titanium(IV) isopropylate; trimethylsilylazide / benzene / 2 h / 5 - 20 &deg;C / Inert atmosphere<br />7.2: 1 h<br />8.1: triethylamine / dichloromethane / 0.5 h / 0 &deg;C / Inert atmosphere<br />9.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 &deg;C / Inert atmosphere<br />9.2: 0.5 h / -78 &deg;C / Inert atmosphere<br />9.3: 0.5 h<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1.1: bromine / tetrahydrofuran / 10 h / 20 &deg;C<br />2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.75 h / -78 &deg;C / Inert atmosphere<br />2.2: 0.5 h / -78 &deg;C / Inert atmosphere<br />2.3: 0.5 h<br /> <br /> &nbsp;