1: 80 percent / tri-n-butyltin hydride; AIBN / toluene / Heating 2: 81 percent / LiAlH4 / tetrahydrofuran / 2 h / Heating View Scheme

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in toluene Barton-McCombie deoxygenation; Heating;

<b>Multi-step reaction with 5 steps<br /> </b>1.1: 83 percent / (DHQ)2PHAL; NMO; OsO₄ / 2-methyl-propan-2-ol; H₂O / 24 h / 20 &deg;C<br />2.1: 90 percent / thionyl chloride; triethylamine / CH₂Cl₂ / 0.75 h / 0 &deg;C<br />3.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 &deg;C<br />4.1: 88 percent / Et₃N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 &deg;C / 760.05 Torr<br />5.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 &deg;C<br />5.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1.1: 80 percent / sodium azide / dimethylformamide / 48 h / 80 &deg;C<br />2.1: 88 percent / Et₃N; hydrogen / Pd/C / ethyl acetate / 12 h / 20 &deg;C / 760.05 Torr<br />3.1: sodium hydride / tetrahydrofuran; various solvent(s) / 0.5 h / 0 &deg;C<br />3.2: 82 percent / tetrahydrofuran; various solvent(s) / 2 h / 0 &deg;C<br /> <br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '1098293', constants.ctx, '0')">carbon disulfide</a>; <a href="#" onclick="return RXDsubstances(event, this, '6849631', constants.ctx, '0')">tert-butyl (1R,2R)-2-methoxycarbonyl-2-hydroxy-1-phenylethylcarbamate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '4122952', constants.ctx, '0')">sodium hydride</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;0.5&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '969135', constants.ctx, '0')">methyl iodide</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=0&deg;C;&nbsp;2&nbsp;h;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;