Multi-step reaction with 14 steps
1.1: sodium azide; trifluoromethylsulfonic anhydride; copper(II) sulfate; triethylamine / acetonitrile; water / 0 - 20 °C
2.1: Amberlite resin (H+) / 72 h / Reflux; Inert atmosphere
3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 20 °C / Inert atmosphere
4.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere
5.1: sodium methylate / methanol / 0 - 20 °C / Inert atmosphere
6.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 20 °C / Inert atmosphere
6.2: 20 °C / Inert atmosphere
7.1: boron trifluoride diethyl etherate; triethylsilane / dichloromethane / 2 h / 0 °C / Inert atmosphere
8.1: dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere
8.2: 2 h / 0 - 20 °C / Inert atmosphere
9.1: pyridine; hydrogen fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
10.1: 2,2,6,6-tetramethyl-piperidine-N-oxyl; [bis(acetoxy)iodo]benzene / dichloromethane; water / 20 °C
11.1: dihydrogen peroxide; lithium hydroxide / water; tetrahydrofuran / -5 - 20 °C
11.2: 0 - 20 °C
12.1: palladium 10% on activated carbon; hydrogen / methanol / 72 h / 20 °C
13.1: triethylamine / water; tetrahydrofuran / 20 °C
14.1: Escherichia coli glycosyltransferase; manganese(ll) chloride / aq. buffer / 20 °C / pH 7.2 / Enzymatic reaction
With
pyridine; triethylsilane; dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium azide; trifluoromethylsulfonic anhydride; [bis(acetoxy)iodo]benzene; palladium 10% on activated carbon; boron trifluoride diethyl etherate; Escherichia coli glycosyltransferase; hydrogen fluoride; hydrogen; dihydrogen peroxide; sodium methylate; sodium hydride; toluene-4-sulfonic acid; copper(II) sulfate; triethylamine; manganese(ll) chloride; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ol500738g