1: Et3N; MeSiCl3 / tetrahydrofuran / 24 h / 60 °C 2: 44 mg / H2O / tetrahydrofuran / 0.5 h 3: pyridine / 2 h / 20 °C View Scheme

<b>Multi-step reaction with 3 steps<br /> </b>1.1: NaHCO₃ / CHCl₃; H₂O / 1 h / 25 &deg;C<br />1.2: 92 percent / pyridine / 12 h / 25 &deg;C<br />2.1: NH₂NH₂*HOAc / dimethylformamide / 4 h / 25 &deg;C<br />2.2: 61 percent / DBU / CH₂Cl₂ / 12 h / 25 &deg;C<br />3.1: 83 percent / TMSOTf / CH₂Cl₂ / 3 h / -30 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: HBr / acetic acid / 1 h / 20 &deg;C<br />2: 74 percent / 4 Angstroem molecular sieves / AgOTf / CH₂Cl₂ / 36 h / 20 &deg;C<br /> <br /> &nbsp;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '19253605', constants.ctx, '0')">4 A molecular sieve</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3598402', constants.ctx, '0')">silver trifluoromethanesulfonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=20&deg;C;&nbsp;Substitution;&nbsp;36&nbsp;h;&nbsp;<br /> &nbsp;

Stage #1: <a href="#" onclick="return RXDsubstances(event, this, '8653203', constants.ctx, '0')">3,4,6-tri-O-acetyl-2-deoxy-2-methoxycarbonyl-amino-α-D-glucopyranosyl trichloroacetimidate</a> <b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1868911', constants.ctx, '0')">trimethylsilyl trifluoromethanesulfonate</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-30&deg;C;&nbsp;Substitution;&nbsp;0.166667&nbsp;h;&nbsp;<br />Stage #2: <a href="#" onclick="return RXDsubstances(event, this, '1098229', constants.ctx, '0')">methanol</a> &nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1730800', constants.ctx, '0')">dichloromethane</a> <br />T=-30 - 20&deg;C;&nbsp;Substitution;&nbsp;3&nbsp;h;&nbsp;&nbsp;Further stages.;&nbsp;<br /> &nbsp;