1: triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 2: tris-[2-carboxyethyl]-phosphine / water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 3: water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere View Scheme

1.1: triethylamine / N,N-dimethyl-formamide / 48 h / 20 °C / Inert atmosphere 2.1: tris-[2-carboxyethyl]-phosphine / water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 3.1: water; acetonitrile / pH 7.4 / aq. phosphate buffer; Inert atmosphere 4.1: sulfuric acid; sodium nitrite / tetrahydrofuran; water / 1 h / 0 °C 4.2: 0 - 20 °C 5.1: dipyridinium dichromate / dichloromethane / 4 h / 20 °C View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '11343357', constants.ctx, '0')">sodium periodate</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3902804', constants.ctx, '0')">silica gel</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, '3587155', constants.ctx, '0')">water</a> <br />T=20&deg;C;&nbsp;0.5&nbsp;h;&nbsp;<br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: triethylamine / dichloromethane / 23 h / 0 - 20 &deg;C / Inert atmosphere<br />2: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 20 &deg;C / Darkness<br />3: sodium periodate; silica gel / tetrahydrofuran; diethyl ether; water / 0.5 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 20 &deg;C / Darkness<br />2: sodium periodate; silica gel / tetrahydrofuran; diethyl ether; water / 0.5 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 8 steps<br /> </b>1.1: sulfuric acid; sodium nitrite / tetrahydrofuran; water / 1 h / 0 &deg;C<br />1.2: 0 - 20 &deg;C<br />2.1: dipyridinium dichromate / dichloromethane / 4 h / 20 &deg;C<br />3.1: magnesium / tetrahydrofuran / 12 h / 20 &deg;C / Inert atmosphere<br />3.2: 2 h / -78 &deg;C / Inert atmosphere<br />4.1: tetrahydrofuran / 18 h / 60 &deg;C / Inert atmosphere<br />5.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 &deg;C / Inert atmosphere<br />6.1: triethylamine / dichloromethane / 23 h / 0 - 20 &deg;C / Inert atmosphere<br />7.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 20 &deg;C / Darkness<br />8.1: sodium periodate; silica gel / tetrahydrofuran; diethyl ether; water / 0.5 h / 20 &deg;C<br /> <br /> &nbsp;

<b>Multi-step reaction with 6 steps<br /> </b>1: N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 0.67 h / 20 &deg;C / Inert atmosphere<br />2: tetrahydrofuran / 18 h / 60 &deg;C / Inert atmosphere<br />3: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 &deg;C / Inert atmosphere<br />4: triethylamine / dichloromethane / 23 h / 0 - 20 &deg;C / Inert atmosphere<br />5: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / acetone / 20 &deg;C / Darkness<br />6: sodium periodate; silica gel / tetrahydrofuran; diethyl ether; water / 0.5 h / 20 &deg;C<br /> <br /> &nbsp;