1: ammonia / methanol / 24 h / 20 °C 2: 24.6 g / TBAF / tetrahydrofuran / 4 h / 20 °C View Scheme

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '906752', constants.ctx, '0')">trimethylsilylacetylene</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1209227', constants.ctx, '0')">n-butyllithium</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '13161774', constants.ctx, '0')">cerium(III) chloride</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=-50&deg;C;&nbsp;2.5&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '9230405', constants.ctx, '0')">N⁴-benzoyl-2'-O-(tert-butyldimethylsilyl)-3'-ketocytidine</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=-65&deg;C;&nbsp;3&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1.1: 96 percent / dioxane; H₂O / 4 h / 90 &deg;C<br />2.1: 82 percent / pyridine / 18 h / 20 &deg;C<br />3.1: AgNO₃; pyridine / tetrahydrofuran / 3 h / 20 &deg;C<br />4.1: 78 percent / CrO₃; pyridine; Ac₂O / CH₂Cl₂ / 1 h / 15 &deg;C<br />5.1: 76 percent / p-TsOH / methanol; CHCl₃ / 0.08 h / 20 &deg;C<br />6.1: CeCl₃; BuLi / tetrahydrofuran; hexane / 2.5 h / -50 &deg;C<br />6.2: 85 percent / tetrahydrofuran; hexane / 3 h / -65 &deg;C<br /> <br /> &nbsp;